About this episode
Eddie Reynolds, founder and CEO of Union Square Consulting, and Joel Arnold, VP of RevOps Strategy at USC, discuss the critical foundations of customer retention in this episode of RevOps Live. With deep expertise in sales operations, implementations, and customer success across organizations like Salesforce and multiple startups, Reynolds and Arnold bring credibility grounded in hands-on experience managing hundreds of customer relationships.
The core insight: Retention success is determined long before renewal dates, and begins the moment a prospect raises their hand—not when they sign. Most companies squander the critical post-sale period through poor handoffs, repeated questioning, and lack of momentum, which erodes trust and creates the impression of organizational chaos. By formalizing documentation, maintaining communication continuity, and involving key stakeholders early, teams can shift from reactive damage control at renewal time to proactive customer advocacy throughout the entire journey.
Reynolds and Arnold reframe retention as a revenue operations challenge that spans sales, marketing, and delivery. They explain how the sales rep's role extends beyond signature, why kickoff timing and clarity matter more than implementation complexity, and how to structure roles and incentives so that retention becomes everyone's priority. The episode focuses specifically on the early customer lifecycle—from sales through onboarding—identifying the exact handoff points where most companies fail and providing tactical fixes that cost little but yield outsized returns in customer satisfaction, referrals, and expansion revenue.
What we cover in this episode
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3:30
Documentation and Information Flow Formalizing the capture of customer insights from sales to delivery and beyond to avoid repetitive questioning.
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8:15
Trust Breakdown and Handoff Failures How poor communication across sales, implementation, and CS functions erodes customer confidence and sets up renewal risk.
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15:30
Go-Live Date Alignment Backing into implementation timelines from customer business goals rather than sales cycle pressure to create realistic expectations.
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22:45
Kickoff Timing and Process Design Scheduling kickoffs predictably, maintaining sales rep involvement, and carving out dedicated time slots for smooth transitions.
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32:00
Sales Rep Involvement and Incentives Why salespeople should remain advocates through go-live and how compensation structures can align accountability for implementation success.
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42:15
Organizational Role Clarity Defining boundaries between account executives, account managers, customer success managers, and renewals roles based on company size and motions.
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52:30
Executive Sponsor Identification Why the executive sponsor is the single most critical stakeholder for implementation success and how to surface them early.
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61:00
Capacity Planning and Territory Design Using usage metrics, contract value, and actual workload to size CSM and account manager territories sustainably.
The lines worth sharing
It's the easiest path to growth for a lot of companies. And how do you get yourself off on the right foot with a customer?
Joel Arnold · 1:45
If you think about this, RevOps is meant to span sales, marketing, and customer success to really deliver this great customer experience.
Eddie Reynolds · 8:50
There's always some nuance there that's not captured. Because what you're trying to do is align expectations.
Eddie Reynolds · 35:20
When you go to the renewal, they're looking at you as a commoditized product. Rather than I have trust that this team is here to support my business.
Eddie Reynolds · 9:15
Common questions from this episode
Why does customer retention matter more than acquisition in downturns?
Retention is the easiest path to growth during economic slowdowns. It costs significantly less to keep existing customers than to acquire new ones, and retention success depends on foundations set during the early sales and onboarding phases, not just at renewal time.
What should I document during the sales process for the delivery team?
Create a one-to-two page templated dossier capturing: why they bought, what success looks like, key metrics, timeline, critical stakeholders, executive sponsor, and any promises made. Store it in your CRM or attached document, and review it before kickoff. Involve implementation and CS teams in designing what information matters.
How long should I wait between contract signing and project kickoff?
Ideally one to two days, though most companies struggle here. Back into the timeline from the customer's go-live date, account for realistic lag time (typically two to four weeks), and carve out dedicated weekday/time slots for kickoffs to reduce scheduling friction and maintain momentum.
Should the sales rep stay involved after contract signature?
Yes, at minimum through go-live as an advocate and translator. They should attend kickoff, clarify any nuances not in written documentation, align stakeholders on expectations, and ensure customer success. Their ongoing involvement should be incentivized—consider delaying commission or tieing comp to go-live milestones or gross margin.
What is the most important customer stakeholder for implementation success?
The executive sponsor is critical. They control resource allocation and can remove blockers. Without their buy-in and active participation, implementations often fail. Identify them early in sales, include them in kickoff, and confirm their understanding of the time and commitment required from their team.
How do I decide when to transition from AE to account manager or CSM?
Consider whether expansion opportunities exist soon after sale, whether the next buyer persona differs, and renewal timeline risks. If opportunities are limited or personas differ, transition earlier. Use capacity models and territory sizing based on bandwidth and opportunity value, not just contract size.
SEO meta description
Eddie Reynolds and Joel Arnold share RevOps best practices for retention. Learn handoffs, kickoff processes, and how to maintain customer trust from sales through onboarding and beyond.
Target keywords
customer retention strategy
RevOps best practices
sales to delivery handoff
customer onboarding process
Eddie Reynolds
Joel Arnold
Union Square Consulting
implementation kickoff
customer success management
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account management
sales compensation for retention
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Read the full transcript · 56 KB
SPEAKER_00Welcome to RevOps Corner, where we talk about how B2B SaaS companies scale through revenue operations by interviewing amazing guests and sharing what we see in the trenches every day here at Union Square Consulting. Welcome everybody to RevOps Live number 24,
EDDIE REYNOLDShacks for retention. Right now in today's economy with the downturn, retention is the most important thing in go-to-market, and it starts long before the renewal date. In this event, we want to share some best practices in RevOps to improve retention, and this is really going to be probably part one of at least a two-part series where we really talk about the beginning stages, the handoff, and the onboarding process. I'm here today. I'm the founder and CEO of Union Square Consulting and here with our VP of RevOps Strategy, Joel Arnold. Joel, thanks for joining me today as always. Yeah, thanks for having me as always. Excited to be here. So Joel, why should people listen today? Well, I mean, because obviously retention is so
JOEL ARNOLDimportant these days. It's the easiest path to growth for a lot of companies. And, you know, what we're going to be talking to you today is how do you get yourself off on the right foot with a customer? Some things to make the user experience or the customer experience easier for everyone. And that's because it's often too late when you get to the point of renewal and you're trying to save somebody. You don't have a lot of levers to pull and the levers that you have might not be so great. So how do you get yourself set up to avoid those problems? And where can you make an impact ahead of that renewal cycle?
SPEAKER_06100%. So before we kick off, we'll just do our normal intro. So if anybody is not familiar with us,
EDDIE REYNOLDSwe are a revenue operations consulting firm. We do both strategy and systems and RevOps. And we put this event on every week or at least as much as we can. We publish this to our podcast, which you can find on Apple and Spotify. Sarah will share links in the chat if you want to access that now. And then we send out a newsletter every Friday, which will also have a reminder to check out the podcast if you want to see the recording here or share it with somebody. Joel and I are going to talk through this topic. We welcome questions from the audience throughout this, although sometimes we don't get a lot of questions. So I'll just keep going through it. And without further ado, we can dive into this. Joel, would you like to kick us off with the first major point you want to share here? Sure. Sure. So in the guise of what can you do ahead of the retention cycle to set up your
JOEL ARNOLDretention program for success, we're going to talk about things from the beginning of the sales cycle onward. It's worth caveating that there are things that you can do with your marketing organization to also tee yourself up for retention. And we're not going to dive into that stuff today, but for example, just making sure that you're targeting the right kinds of customers, the customers that you're going
JOEL ARNOLDto be providing a lot of value to because they just fit with your product and services, that can also, and is a major part of making sure that they stick with you in the long run. But today, when we talk about what you can do to set yourself up for success, we're going to begin by documenting learnings that we have during the sales cycle. And this is, it seems hopefully obvious to a degree, but really what we want to do is formalize this process because what we're trying to avoid is, you know, at the time of handoff post-contracts to, let's say the person doing your kickoff, maybe your implementation or delivery leader. You don't want them asking the same questions that you just got done answering during the sales process. And then again, they go live and they get handed off to account manager or a customer success manager as the owner of that relationship. And then they ask again, the same questions that they're asked during the kickoff, which they were asked during the sales process. And so this, the easiest thing to do to make the customer's experience be better is to avoid repeating yourself as an organization over and over and over. And it gives off the impression that you also don't have your, your docs in a row on, on your side of the house. So what we're suggesting, and this could be informal, it can be as simple as a document that you create, just have something in place where you're capturing in a templated and consistent way, common questions that are captured during the sales process that are useful for teams later on in the journey for the customer. So what we would suggest in this part, at least just super tactically is talk to your implementation team, talk to your customer success team, figure out the key points of information that they're going to want to know from every customer. Things like, why did you buy? Why are you interested? What does success look like for you, et cetera? Bring these stakeholders together and let them to help you to design whatever that
JOEL ARNOLDtemplate is going to look like. Obviously you're using your sales cycle to capture a lot of these items already, but occasionally they'll have you point to the sales person and say, "Hey, going through this process, could you make sure that you please document this extra thing that wasn't necessarily part of the old sales cycle?" And I think with, with a grain of salt, that's totally reasonable to ask of a sales organization. We want to make this thing, whatever it is visible, whether it's a set of fields or a section carved out in your CRM, let's say the opportunity page, or if it's a template, a document that you attached to the opportunity. Just make sure that it's shared with delivery, it's in a visible place, it's part of your handoff processes internally and your kickoff processes, et cetera, and then continue to refine
JOEL ARNOLDit, continue to refine it. It should not be more than a page or two, ideally, but just that amount of information is going to avoid that, again, repetitive nature that making you seem as though you don't have your stuff in order. And it's going to really help not only improve the customer experience, but also speed up things like the implementation. Yeah, I think you shared a lot of really great
EDDIE REYNOLDSpoints there, Joel. I've been on both sides of the table of this for 10 to 12 years, depending on where you draw the line. So 10 years ago, I started as an account executive at Salesforce, and I spent three years there where I was on the sales side and then handing my customers over to external implementation partners. Over the past six years at Union Square Consulting, we've been on the other side of that table. And prior to Salesforce, I worked at a small startup where we did our own implementations in-house. And this was a startup on the Salesforce platform. So pretty Salesforce heavy here. And everything that you shared is a completely on point with what I've experienced over those 10 to 12 years in that you really, like, if you think about this, RevOps is meant to span sales, marketing, and customer success to really deliver this great customer experience. And that starts with the promise that marketing makes. So if you think about it, somebody goes to the website and they see a book, a demo that's put out there by marketing, they then go through the funnel and they get in front of an SDR who then qualifies them, ask them a bunch of questions, maybe doesn't even understand the limited amount of information they shared in a form. Then they pass them over to an account executive. There's a breakdown often where the, the account executive just asked the same questions again. So then they finally signed the contract and they get handed over to implementations. And now they have to do it again. By this point, they're so incredibly frustrated. And there's a lot of trust that's broken down because at the end of the day, customers want to feel heard. They want to feel like you understand them and their business and how to help them. And the more breakdowns you have in that communication process, the less trust is going to be built. And so when you go to the renewal, they're looking at you as a commoditized product. And they're asking, what does this product do for me? Rather than I have trust that this team is here to support my business. And there's a really big difference between those two things. And so when I was at Salesforce, it was very difficult because we worked with external partners. And so we would have to work really carefully to bring the right partner in, and we would often bring them in during that sales process. And so by the time we got ready to go to contracting, the customer already had a really good understanding of what the implementation process was going to be. And I was clear that the implementation partner would understand the customer's needs and be able to regurgitate that back to them in a clear way so that I could have the best assurance that we'd have a smooth process. When I transitioned to starting Union Square Consulting, where I'm still doing all the sales and marketing here, not all of it, Joel, you're helping out a lot with this stuff as is Sarah now, but for a while, it was like that. And now I closed the deal and handed off to you and Jerry and the Restored Delivery team. We have formalized this process where we have these detailed notes and quip. We pass those over and have the delivery team review those notes thoroughly. Then we have an internal kickoff call so that everybody is completely aligned and I'm able to communicate all the things that are not inside of those notes, what the top priorities are, what the things are that they should look out for, the nuances that they should be paying attention to. And some of those are outlined in those notes because those are key things that we're always looking for. And then also joining in on that kickoff call to make sure that there's a smooth transition and nothing is missed before I hand the account over. And when I worked at Alt Via, this small startup, it was a very, very similar process to this. And we had a really high touch onboarding practice where customers really felt like they were heard and taken care of. And that all stemmed from the amount of time and effort that went into making sure that that communication process was streamlined. I can take this a step further and say that Salesforce also did what you're advocating Joel and putting all of these fields in Salesforce. And I would get a lot of pushback as an account executive, even bringing in colleagues on the sales team, such as a sales engineer into the sales process. If I didn't have my ducks in a row in the Salesforce opportunity filled out because they would say, look, I'm not going to play telephone with you. If you're not going to put the right information in the right place for me to understand this account, I'm not going to take this meeting. And so that created rigor around documenting our findings so that we would have a smooth process, especially as we brought in lots of different stakeholders, both on the customer side and on our side.
JOEL ARNOLDYeah. I think the classic story is, you know, you sell something, you're a customer and then you wait two or three days before anyone gets ahold of you to say, Hey, welcome, or let's get that kickoff schedule. Then you wait a couple of weeks, maybe a month for the vendor to get all of their handoffs done and to like find time on everyone's calendar because everyone's busy. And then you go through this implementation process and they're at their kickoff meeting begins by asking you the same frigging questions that you just answered during the sales process. And it's just, and then there's a handoff at the end and you're not quite sure who to reach out to. So you go back to your salesperson and maybe the customer has told you, Oh, from now on reach out to your CSM, but you're just like, you've got a relationship with the salesperson. So you kind of ignore them. Like, Hey, these guys aren't doing this. You go over to your salesperson. It's like, Hey, can you help me out here or whatever? And it just becomes this garbled mess. And it's a terrible experience. And when you think about revenue operations, you know, it'd be marketing and sales and CS and where does implementation come in here? Because it's like this couple week or maybe a month long thing that's sort of inserted between sales and CS that like, doesn't get any
JOEL ARNOLDlove. And what we're trying to do is just, at least with this is call out ways that we can make that easier because I do think it fits under the purview of a brev ops. If you're, if you're really concerned about retention, not just CS, but like retention as a, as a topic, you really got to nail this stuff.
JOEL ARNOLDAnd it's a great way to kind of keep momentum going because momentum is really important when you're in the sales process. And it's just as important post-sale to keep that momentum going, or else you're not going to get the adoption that you want. You're not going to maintain that trust, that relationship. You're not going to have the opportunity to grow if you leave a bad taste in
JOEL ARNOLDpeople's mouth. So this is really, really important stuff that, you know, when you're going through the
JOEL ARNOLDsales process, you're concerned with selling and you're concerned with getting that contract across the line. You also need to be concerned about what's going to happen after the contract is signed.
SPEAKER_16And so that's just, that's kind of what we're diving into today. And hopefully, hopefully that'll make sense. Yeah. Well, this is also a sales opportunity,
EDDIE REYNOLDSright? So taking it back to the very beginning stages, no customer cares about, well, we need to sign this contract by X date. That is a hundred percent on the salesperson, right? I need to close my deal by the end of quarter, by the end of the month. And then we'll throw out discounts a lot of times. And I've been sitting in sales calls with Salesforce AEs for the past number of years, hundreds of them that I've worked with. And some are good. Some are, you know, need room for improvement. And I can't tell you how many times I've sat in a call and I've heard an AE try to push a date on somebody and say, look, like, you know, we need to get this signed by the end of the month. And I'm sitting there and thinking I've been in every meeting that you've had with this, this prospect, there is no interest on their end whatsoever in getting this signed. And they're just pushing it down their throat. And what you need to do instead is you need to back into the go live date. That's what they care about. What they care about is when am I going to have this solution in place and how is this going to help me reach my objective? Right? And so oftentimes when you think about somebody that's really motivated to sign a contract, they say, okay, like we're buying Salesforce because we're onboarding a new sales team and we have to have all these people up and running by, you know, August 1st, whatever. Okay, great. So we have to have Salesforce working by August 1st. How long does that implementation take? Okay, let's say it takes six weeks. Great. All right. Now, there is oftentimes lag time between the time that you sign a contract and the time you actually kick off the project. I think it's wholly unrealistic to expect that you can sign on Friday and start on Monday morning. Although everybody wants to do that. So I think it's, it's really good for the sales rep to explain that in the first call or two and say, you know, typically we have a lag time of X number of weeks. So we need to add that into our timeline. So if you want to be up and running by August 1st, we need to have a decision made by this date. What are the steps that we need to take in order for you to feel comfortable making a yes, no decision so that you can have the solution that you want in place on the date that you want it. Now you've created a mutual evaluation plan and really create alignment with that customer and also avoided the surprise that now they're upset that they have to wait three weeks for the implementation to start because once the contract is signed, that's when resources get booked. And now you really have this tight integration with your customer. And I found that to be a really powerful tool to get deals closed on time that not only helps sales, but also then helps with the onboarding process and the customer experience. Yeah. And that's a great segue into
JOEL ARNOLDour next topic because it is basically that it's it's have a tight kickoff process. And the sales process is the thing that tees up a good kickoff process and the good kickoff process with the
JOEL ARNOLDhandoffs and the communication and the project management that goes along with it is really that
JOEL ARNOLDplace where you prove yourself as an organization and leave that good taste in someone's mouth. So kind of as we as we've mentioned, you know, this this is a really important step, a really important step that is often neglected. So some pointers for how to do this the right way is make sure that you have a clear and hopefully concise because you don't want to waste anyone's time. You want to be efficient about this. Have a clear and concise process internally for like handing off or knowledge transferring all the things that you learned during the sales process to the team that's actually going to be doing the delivery. So if one, it's that document, that dossier that you've been putting together either in your CRM or in an attached document or something like that where it's visible to everybody. Hey, let's go review this. You mentioned internal notes that we have at USC. There's a place that we store all the notes about the customer. What does success look like? What are the key metrics? What's their timeline? Why did they buy? Why did they choose us versus somebody else? Et cetera. And then I, I know it's very, very difficult to have somebody sign on Friday and kick off on Monday, like you mentioned, but that should be the aim. It should not take three, four weeks to get something on the schedule because of that momentum piece. So we are going to try and do some things that, that help you to get that set up a little bit. And one of my suggestions is kickoff timing is so important that you should work with your implementation team to carve out specific days and times of the week where you can do kickoffs. Like if it requires three people to do a kickoff, make sure all three of those people keep Wednesday morning available, keep Monday afternoon available, whatever it is that makes sense for you so that you can get that kickoff scheduled at least as rapidly as possible. Um, I think that kind of speaks for itself for why you want to do that. Um, well, let me, let me chime in here, Joel. I think that's a really great point. And the
EDDIE REYNOLDSperspective I've had is only in these really complex integrations like Salesforce, right? I know many companies have a really standard implementation and it's kind of like, they've got X number of people and they all do the same thing and they run through the same process. And I think that that's very streamlined. And at the same time, like I've always told people at USC that, you know, we need six weeks to kick off. In reality, most of the time we sign on Friday and start on Monday, right? We're scrambling. We're doing exactly what you're talking about. I'm just very hesitant to ever promise that to somebody. Right. But to your point, that's what everybody wants. And so oftentimes we're bringing in the implementations team into the sales conversation. And it was the same when I was an AE at Salesforce. We're working with implementation partners. Hey, they really, we think this is going to get signed on Friday. They want to start the following week. Do you think you can do this? They're starting to align resources. They're starting to like, look at schedules. But to your point, if you have a more streamlined process and you can just say, okay, like on this day of the week, that's when we do kickoffs. I really, really love that concept. Yeah. Yeah. It's, there's actually a lot of parallels
JOEL ARNOLDif you really think about it between when someone raises their hand, Hey, I wanted to get a demo at the beginning of the sales process and your speed and quality to follow up on that being a key differentiator for you as a sales organization, as a company, just kind of giving the impression that you have your ducks in a row and you care about the person's time to parallels to the post-contract process where you send a welcome email. That's also a pointer you should probably do. Make sure you send a welcome email, taking off quickly, maintaining that momentum, doing it in a coordinated way and making sure that you are internally. So the
JOEL ARNOLDcustomer can actually tell informing the delivery team about that customer, what, you know, what are their key metrics? What do they care about? Why did they buy? And so what ends up happening is you have this sort of like quick roll over to the next thing and just consistently leaving a good impression. And what this is going to tee you up for specifically in the future is speed to referral or speed to referenceability. If you, if you have a poor kickoff and a poor handover to the account manager or CS team
JOEL ARNOLDlater, et cetera, et cetera, you may never get a referral from that customer that had a bad experience. You also might have, if even if the CS and AM team and adoption happens thereafter, even after a clunky
JOEL ARNOLDkickoff and implementation, you might have to wait for six months before the customer feels comfortable referring someone to you or being a reference for somebody who's going through the sales process. And what you're, what you want to do is if you have an excellent sales process, if you have an excellent kickoff and handoff, if the C, if the CX component of all of this is very strong right away, man, you can get a month into this thing post go live, man, they're, they're chomping at the bit to refer you. So not only have you gotten that reference and that referral at all, but you've gotten it a lot
JOEL ARNOLDfaster. And so this stuff sort of just builds upon itself and leads to more sales in the future as well. So there is a real tangible benefit to doing all this stuff. It's not just like speed to delivery and speed to value or whatever. There's other things going on here. And all of it, all of it
JOEL ARNOLDis improved by kicking up quickly, having good handoffs, et cetera, et cetera.
EDDIE REYNOLDSAnd so let's dive into the weeds on some of this. Like, I really love the point that you highlighted about having the data in the CRM. And we also, we use Quip, it's a sales source product, but you know, Evernote, whatever other tool you want to use, it's very similar. I think that there's this balance that you want to have with, you want the implementation team to have perfect data and information. You want the customer to have the best experience. And at the same time, every sales rep in the world wants to sign the deal and then snap of a finger, move on, right? Like I am out, right? And that is exactly what I do here at USC. And the benefit here is, is the second that the deal is closed, I mark it closed in Salesforce. There's an email that goes out to accounting. There's an email that goes out to delivery and they have their playbook with the step-by-step things that they need to do. They send the welcome email to the customer. Hey, you know, welcome to Union Square Consulting. I want to schedule your kickoff. They know who the contact is because we have that data in Salesforce. They know like key criteria. What are the specific things that we need to look for in the sales process? And usually in our case, like the delivery team has been involved in the sales process. So they already know a lot and that's very key. But even if not, there's key data points that we're looking for that the delivery team has to know. And then they're also scheduling that internal handoff meeting immediately between closing the deal and the customer kickoff. And so I don't have to think about it. It's like, okay, you've got Salesforce. You've got the quip notes. You just put time on my calendar and now I can move on to the next thing, but still be sure that you have all the information necessary. And then I come to the kickoff call and if something slips through the cracks there, that's a third checkpoint that I can pipe up and say, oh no, wait, wait, Joel, Jerry, actually, what's really important to them is X, Y, Z. And then turn to the customer and say, can you confirm that for me? So now they feel like they're being heard. They feel like nothing is slipping through the cracks. And then I can check out after that call and feel comfortable that that customer is not going to feel like they just got handed off, that they feel like they've had a smooth transition.
JOEL ARNOLDYeah. Yeah. Yeah. You mentioned a couple of things I want to, I want to like double down on. Don't allow your salesperson to just like check out and not care about this person anymore and go
JOEL ARNOLDfocus on prospecting. That is that we're not there yet. You need to make sure that the salesperson or at minimum, somebody who is involved in the sale, it could, you could have a sales motion where you have
JOEL ARNOLDmultiple people involved in a sale, sales engineer, a solutions consultant, something like that. Somebody that the customer knows from the sales process needs to be a day kickoff call.
JOEL ARNOLDSomeone who knows the customer inside and out. So when it comes to the things, which there will inevitably be questions, conversation points, et cetera, that are not captured in your standardized
JOEL ARNOLDdocumentation that are important to that deal. Somebody from your side that can be the advocate, the translator, the person that can sort of pipe it, pipe up and answer questions and make sure things are on the right track. So that the customer doesn't have to, again, get in that situation where they're sort of forced to say, actually, your team promised that we were going to do that thing or that way. Hold on. That doesn't make any sense. Like, as long as there's somebody on your side that has held their hand for a long time, you'll be able to jump in there and make sure that there's no gotchas, no confusion, that the transitions are easy. So make sure that you have somebody from the
JOEL ARNOLDsales process invited to kickoff call, attend the kickoff call, and act as a liaison and a translator and an advocate for the customer. Yeah, I think that that's so important because what I have found
EDDIE REYNOLDSis no matter how much we talk internally and what information is shared, there's always some nuance there that's not captured. Because what you're trying to do is align expectations, right? You got to keep in mind, like, if I'm closing a deal, I'm working with usually one single stakeholder. Yes, there's multiple people involved in the decision, but there's usually a champion. There's one person that I have my main point of contact in. And then we go to the kickoff call and they loop in a bunch of other people, some of whom have never been involved in the process, and they have a totally different set of expectations. And a lot of times it's like, I'll be going through the sales process and I know that I've told this person, hey, by the way, like, don't expect this, don't expect that, like, trying to temper their expectations. And then we go into the kickoff call. And that is our opportunity to level set with the entire team, their team and our team, and get everybody on the same page with what reasonable expectations are. Because in implementations, like the most difficult thing is, is that people have unrealistic expectations. Customers think that we can work miracles while they're sort of like checked out, not showing up to meetings on time, X, Y, Z, and they can get the result they want without putting in the required effort. And I think that that kickoff call is where it's really critical to lay the groundwork to say, in order for you to get the outcome that you want, we have to do X, Y, Z. And to reiterate that as the salesperson, so they don't feel like, oh my God, I'm now being asked to do something by a new person. And I had all these promises made to me by the sales rep that this was going to be easy. Yeah, you need the sales rep there. There's one thing before we dive
JOEL ARNOLDinto talking deeper about sales rep involvement is the pre-tickoff call internal knowledge transfer
JOEL ARNOLDprocess. So this is something we get asked about a lot. What would you recommend? It unfortunately depends. It can be for a super-duper transactional business with an easy implementation that's cookie cutter, just like a consistent approach and you get it live in three days kind of a thing. And those businesses exist and they're great. You don't necessarily need to have a meeting about knowledge transfer. But most of us are going to have a more complicated sale all the way up to like an enterprise deal that might have customer development involved and all kinds of different stakeholders. And so your standard deal may... capturing the information about the standard deal is really important, but it may not be sufficient. So you would probably want to have a meeting with the key stakeholders. What I would suggest without this is make sure that you're tailoring this to your business and try to have as few invitees to that meeting as possible. Because what you'll find is that people will complain if they feel like the time is wasted. And so ideally on the implementation side, there's at least a point person or a single project manager or delivery manager overseeing a team of project managers that you could brief on all this stuff will be in attendance and sort of leading the conversation at the kickoff. And that's who it may just be salesperson and that person that might be enough for you.
SPEAKER_26Yeah, I think that that raises a really good point. I mean, when you think about an implementation,
EDDIE REYNOLDSthere's usually two, three, four people that are really intimately involved in the project. And there can be dozens of others that are sort of tertiarily involved. And if you invite all of those folks to the first call, it can become quite a train wreck to your point. Like a lot of people feel like their time wasn't well used. And at the same time, one of the most important people in this process is the executive sponsor. And the reason the executive sponsor is so critical to an implementation is because they're the person on the other end that ultimately decides what resources get allocated to a project. So for example, what we've seen so many times with Salesforce implementations that go south is that, you know, somebody like a junior employee, an office manager, an EA, someone like that is tasked with running the Salesforce implementation. And then at the same time, their boss is overloading them with other work. And so they actually don't even have the proper amount of time to work with the implementation team to make this a success. And then meanwhile, they have to go to other people on the team, the users, the managers, et cetera, and get their buy-in to support the initiative and to participate appropriately. And those people are maybe not bought in and they're just kind of pushing back on somebody that doesn't have any power over them in the organization. And this always goes back to the executive sponsor. And so if you don't have the executive sponsor involved in the implementation, then this is oftentimes where these fail. And I can only speak from the perspective of my experience with Salesforce, but covering about 300 customers in my time at Salesforce and hundreds more since I left, I really can't think of a single example where we had an executive sponsor that was completely bought in and they were not able to get to their end destination of having a successful implementation. Half of my customers did not reach that destination. Half of them were paying for Salesforce and not utilizing it correctly. And every single time that I called into that company to try to find out what was going on, I found out that there was an executive sponsor that was completely checked out. Yeah. It's not surprising. And it's one of those things that you want to make sure you're
JOEL ARNOLDdocumenting early on because part of your sales process is discovering who that person is, right? Making sure that you're getting in front of them. And so having that as a contact attached to an opportunity in Salesforce, CRM, whatever, and part of that dossier that you're keeping about an opportunity is incredibly important as well as part of the kickoff process. You want to make sure that you're confirming who the different roles of the people are on the customer side, who's the technical lead, who's the point person from the business side, who's the executive sponsor, who's the point of escalation, et cetera. I'm fairly certain almost everybody's implementation team cares about this stuff anyway, but it's worthwhile just making sure that that stuff is in place as well.
EDDIE REYNOLDSYeah. And then what I would add to this is, is that if you get the executive sponsor to that kickoff meeting, then you think about who are the other key stakeholders you need. And then at least in our experience, at least for Salesforce, the objective of that meeting is really to set the foundation for the project. And then you can go in and do discovery and drill in deeper with other key stakeholders that don't necessarily need to be in that initial meeting. But what you're really trying to accomplish is to say that like, we have a plan and the executive sponsor knows what is required of their team in order to have a successful implementation. The project manager on their end, the technical lead, oftentimes the same person understands what is required of them. And they both hear it at the same time. They're like, Hey, this is not something you can devote 15 minutes a week to and expect success. Like we're going to need X number of hours a week of you. We need to have a meeting with you every Monday and Friday or whatever it is. And everybody that is important to that project is hearing that. And we're all on the same page versus not having those people in the meeting. And we're playing telephone, and this is where we see these things break down.
JOEL ARNOLDYeah. And speaking of avoiding at least playing telephone, because that's, that's huge. And we mentioned that you should keep reps involved. There's a lot of questions about how you do that. We're going to talk for the rest of this conversation about the reps role and when, what they should be doing, how the system, meaning your organization should be facilitating their involvement and then, you know, how to transition them out and when to. So the first thing is, obviously we've already mentioned, keep reps involved, but at least until when my, my contention here is at least until go later. Now you're not expecting the sales rep to be the, the project manager. I think I have been in a couple of organizations where there is assumption that the person driving the project forward on the implementation side as has been the salesperson that sold it. That's not fair. That's not a good use of your salesperson's time. There should be people on the delivery team that are, you know, taking the reins there. But as we mentioned before, the salesperson is an advocate for not only the customer, but also the project in general, right? They sold it based upon the assumption that this is good business and that there's a task that we're trying to achieve, a pain that we're trying to alleviate. And so they, they are sort of the champion internally for this. So if we talk about executive sponsor, they're kind of like that you expect executive sponsor internally. And so you want them involved and this could, and probably should, if you see this as an, as an issue, be tied in some way to the compensation that they receive. Now, maybe Eddie disagrees with this, having been a former salesperson, but my assumption is it. Oh, well, that's great. That's great. But like every salesperson I know is trying to sell good business. They're trying to sell a deal that's actually like achievable. So the last thing you want to do is allow reps to, to walk away and just kind of like walk their hands and move on to the next thing and not care about whether or not the thing that they promised
JOEL ARNOLDto deliver on behalf of the organization that it's actually delivered. Yeah. I mean, I'd love to dive into that just for a moment, if that's okay.
EDDIE REYNOLDSYeah, go for it. I completely agree with you. And I think that, you know, this isn't a webinar or an event on, on, on comp, but incentives really, really matter. And I will say sometimes people want to do what's right for the customer independent of incentives. When I worked at Salesforce, what I saw is that everybody was really trained to say like, look, we need to make this implementation a success because we know that we can't upsell that customer six months later, if we don't get the right implementation partner in place and get people lined up correctly and hand this off correctly. However, I also saw some other reps that realized, look, who cares? Like this customer is not going to be my customer in six months. So let me just jam it in and get it closed and tell them what they need to hear and move on because there was no financial incentive to care about the success of that implementation beyond the ability to upsell them six months later. And I am a firm believer that if you have a customer that isn't successful onboarding on the platform and then they atrit or what have you, RevOps should really be thinking about how to design incentive compensation plans that align with the outcome that you want to achieve. And I think that most good sales reps will want to make sure that that customer is successful if they have some incentive to do so. And even if not, but the incentive really matters in my opinion. I think it definitely matters and it could come in a lot of forms. So if you're thinking about
JOEL ARNOLDcompensation, you may delay payments of commissions until something goes live. I've seen that happen.
JOEL ARNOLDYou may have commissions earned be a certain amount up front and then the remaining amount upon go live or upon some milestone. So there's a lot of different ways that you can do it. I just, I feel very strongly that someone who's in the sales position needs to have connections to the deal as on an ongoing basis, even if they do not own that customer relationship in an official sales capacity, post-sale.
JOEL ARNOLDYeah. And we've even done things in the past with like paying people on,
SPEAKER_06on the gross margin. So like if, for example, the sales rep, like over promises and then the
EDDIE REYNOLDSimplementation team ends up having to do double the amount of work because they're meeting promises that weren't in line with what was sold. Then now the rep gets penalized for that. Yeah. It's, it's difficult to pay on gross margin. I would love to pay on gross margin. If I'm a
JOEL ARNOLDrev ops leader, it's, it requires you to be able to calculate gross margins and margins in sort of a live way based on like having accurate PNLs, et cetera. A lot of early stage companies don't have the sophistication in place to handle that. So in the absence of being able to do that, which I do, you know, that's the Holy grail and the absence of being able to do that. There are still other things that you can do to make sure that just, there's an alignment there with your sales team.
EDDIE REYNOLDSYep. Well, cool. Well, let's not spend too much time on that. Cause I know that's not the point of this event, but it's a hot topic. Yeah, no worries. It kind of does translate into the next
JOEL ARNOLDtopic, which is what are your rules and engagement for when a salesperson rolls off, if they roll off at all. And so, you know, this is going to be different for each company, but so where there's not like one hard and fast rule, but here are some things to think about, you know, the traditional thing is either the customer gets live and the salesperson rolls off immediately or the salesperson holds onto the account for a period of time, let's say a year or the person holds onto the account forever. Those are the most common sort of three different flavors of this. So some things to consider is does a product set lend itself to being upsold or have initial sales done shortly after the sale, the initial sale. So obviously if, if there are opportunities right away to sell more things, then it's probably worthwhile potentially holding onto that salesperson and having them own it through that next sales cycle. If, if not, then, you know, it may be worthwhile to just, you know, eject that salesperson from that situation, bring in an account manager or somebody who's more into the retention side of the business and expansion side of the business is more of a specialist and, and transition earlier. So to speak, you don't want AEs waiting around sitting around waiting for the next thing, you know, six months, nine months, 12 months down the line. So I think that that makes sense. The second thing is a subsequent sale with the same buyer and persona as the initial sale. So if your flagship product has a different persona, and let's say that's a thing that's typically sold up front, and then the expansion products that are after are with a different buyer, with different pain,
JOEL ARNOLDwith different needs, et cetera, then the salesperson has to learn how to, you know,
JOEL ARNOLDget conversations with those people, how to pitch that, how to frame that, how to propose that, the whole different buying cycle with a different person. It may not be worth the time to have that same salesperson having to learn two different sales motions, because that's just a very difficult thing to do. So in that case, it may be worthwhile transitioning earlier. And then the last thing is like, obviously keep in the back of your mind the renewal, because that's, that's the most important thing is the retention part of this. So if an implementation is long, and then the expansion sales cycle is a long time, and then eventually you're kind of like plotting up against the renewal, and you could potentially put that into a delay or jeopardy or clouding the clouding things up about who owns that, then don't, don't play that game. Introduce somebody early enough in the process that they're going to be able to have an impact and be able to manage the renewal, because my assumption is
JOEL ARNOLDthat you're not going to have your AEs doing renewals as well. So those are the things that I would think about.
EDDIE REYNOLDSYeah, and this is a perfect transition into what's probably our next event and our next newsletter. And I'm writing right now, which is on like what these roles are, right? And so I use Salesforce as the example, and I use it with hesitancy, because startups will say, whoa, whoa, whoa, like, we can't build a team like Salesforce. That's ridiculous. And I say, okay, that's fair, right? But if you think about each thing that each person is doing, you have to ask yourself, do we want somebody doing that? Or do we not want somebody doing that? Right? You think about each one of these roles, right? And at Salesforce, the account executives are also the account managers. So they do new business and existing for the most part. Then you have, in addition to an account manager post-sale, you have a renewals manager who's dedicated just to that renewal. Then you also have a customer success manager who is really there for monitoring customer health. And then of course, you have customer service reps, like the entire customer service organization, right? And then you also have product specialists and sales engineers and all these other folks, right? So when you think about taking that down to a small startup, then you have to ask like, do we want one person performing all of those roles? Do we want two people, you know, breaking those roles apart? And where I think it really makes sense is first drawing a line between, you know, is this a sales activity or is this not a sales activity, right? So a renewal is a great example. A renewal can be either. So what I saw when I was at Salesforce is I would reach out to one customer and they would say, Hey, look, like we don't have any interest in looking at any other products or services. We are just going to renew our contract as is. We want to haggle with you over the contract terms, our payment terms, what the price is, et cetera. And with that, as the account manager, you're sitting there looking at this and you're saying, okay, there is nothing for me to do here. So why don't I just let the renewals manager handle that? At the same time, you talk to a different customer and you have, you can use the renewal as a sales opportunity. And you can say, look, there's an opportunity to get better pricing upon renewal. I know that you guys are potentially interested in X, Y, Z. Can we explore that well ahead of the renewal and package this together and give you better pricing? And so you really have to make a judgment call on whether or not this is worth the time of somebody who is a sales rep versus a renewals manager, which by the way, at Salesforce, these are also salespeople, but they're just like a little bit different type of salesperson. Then you have customer success, right? And so again, I'm thinking of a customer success manager solely from the perspective of customer health, not what in a lot of organizations they are, which is also customer service, which is also onboarding and implementations is also a lot of different things. But who is responsible in the organization for monitoring customer health and doing something about it, right? Now, a lot of times in my experience, those folks are not necessarily salespeople. And so they might be really good once they get in front of a customer at helping them, but they might not be the person that's going to go and call that executive sponsor and beat the door down and say, hey, you really need to take a meeting because you guys are not on path to have success here. And I want to fix that for you. And so what I experienced at Salesforce was, is I would go kick that door in and then I would get them to commit to say, yes, we'd like to fix this problem. I'd say, great. Well, now I don't want to hold your hand for the next three months and teach you how to run reports in Salesforce and how to get, you know, like in front of the implementation team and fix all these problems. Like that's not worth my time. But the CSM, that's like, what they specialize in. So get them in front of them and now the CSM can run with it. And so my advice to startups is to like break each of these roles down and ask like, well, maybe we have a CSM that does customer health and customer service and onboarding and they do renewals. And we have an account executive that also is an account manager. Okay. Now we have two people covering all these roles. Well, at least we have rules of engagement. We know who's doing what, and now we can build a process around it. Yeah. In my experience, especially in companies,
SPEAKER_28I would say smaller than 25 million in ARR, you never have all those different roles. You never,
JOEL ARNOLDnever, never do. You know, I've seen this sort of yo-yo thing happening and this happens about it on a two year cycle. It's like, we have a CSM who's involved with maybe some customer support, but they're kind of the customer health person, but then they're also in charge of renewals. So there's this hybrid account manager, CSM renewal manager thing going on. And then eventually they
JOEL ARNOLDrealize that, oh my gosh, well, our, there's a lot more white space here. That's not being attacked. We're not really, they don't have the sales skills. They're not drumming up new business,
JOEL ARNOLDet cetera. And so let's split these things apart and have a sales person on our current existing customer base. And let's just let CMs, CSMs be the, be the person, make sure that customers are happy and utilizing the product and are being successful. And then over time you realize, oh, we're spending way too much money on having two people in the same account. So let's, let's push those roles back together. Let's just hire different people. And so you have this sort of long-term, like, who do we hire? What roles are there in a company? And I just like, they spread them apart and they smash them
JOEL ARNOLDtogether. They split them apart and they smash them together based on whatever the best practice that sure is in that space. And I don't think that's a healthy place to put this. We're getting a question in here. How does the size of your customer play into this? If your average contract size is 150. Do we want to invite James on to ask the question?
SPEAKER_06Yeah. James, go for it. All right. Can you guys hear me? Okay. I'm driving to LA,
OTHER GUESTso it might be a bit hard to get the audio, right? No, I can hear you just fine. All right. Awesome. Yeah. So I guess the, the question is, you know, deal with customers, some contracts are on the, on the smaller side, kind of the 15 to $70,000 a year point, and a CSM and AE kind of makes sense to manage that. But on those larger contracts, you know, 150 K plus where implementation might take longer and then the process is a bit more complicated, you know, even if the company is below that 25 mil ARR level, would you say dividing that role, those roles up a little bit more makes sense in that scenario? Do you have clear usage metrics?
JOEL ARNOLDCan you tell how successful the customer is or how often they're using the product?
OTHER GUESTYeah, we can. So, so we break it down by health scores. So we have a bunch of different factors to play into it, but yeah, our platform informs, you know, how much they're using it. And then we have metrics from things like support tickets and engagement with their CSM and onboarding manager and things like that. All right. Tell me about the products that they would be selling as an
JOEL ARNOLDexpansion. Are they the same buyer? Is it like more licenses, et cetera, or is it potentially a
JOEL ARNOLDdifferent department where they would have a different buyer? Potentially a different department
OTHER GUESTwith a, with a slightly different buyer. Yeah. Okay. Okay. Are your renewal rates pretty solid? Good question. So far, yes. We're a pretty young company and average contracts are about three years. So we're coming up to a bunch of big renewals this year, kind of for the first time and over the next couple of years. So it's kind of a point for us. Okay. Last question. I promise. Do you have
JOEL ARNOLDa sense for the capacity of each of these different roles, like how many accounts they can manage? We do. Yeah. So we, we kind of tie it to the value of that, that book of business for a customer
OTHER GUESTsuccess. Okay. Okay. All right. In that case, while you could, you could do it anyway, either way,
SPEAKER_28I think that you've got a very strong base for a CSM for certain, I think the, the case for the account
JOEL ARNOLDmanagers as a separate entity makes sense because of that separate buyer. What I don't necessarily think would make any sense at all would be having the initial salesperson involved in the sale post sale. So just sort of getting that out there beyond that, if the account is large enough and there's enough opportunity that I don't see a reason why the account manager role couldn't exist as a separated role from the CSM. I think that, I think that makes sense. It would just be something where you would probably have different territories in the CSM simply because I don't think the size of the existing deal is a driver for the size of the territory for the account manager. So I would see the CSM being in charge of finding opportunistic leads and referring them to a salesperson and that being their primary aim. As far as who runs the renewal, I think it might make sense to have the CSM be the point person for that because your account manager is going to be more looking for opportunities and finding them and going after the accounts that are most high propensity to have upsell opportunities where they're not going to necessarily dive in is on every single account. So they might not even touch, you know, 75% of the accounts that are in the system.
OTHER GUESTOkay. Awesome. That makes sense. So I guess to, to distill that, that basically based on the opportunity value, less so the current value is where we would be focusing on whether or not on the managers actually taking into those accounts. For the account manager role, yes. For the, for this
JOEL ARNOLDcustomer success manager, if the amount of bandwidth needed to service that account is based on the size of the deal in question, then yeah, size of a book of business really is, is a good measure there. If it just happens to be a bigger customer, but it's no more difficult to service a million dollar customer versus a hundred thousand dollar customer, then the size of that book of business may not be the metric that you want to use for CSMs. You may want to look at more of a like capacity model from how much work can they get done? How many clients can they handle as a, you know, instead of dollars? That makes sense. Thank you so much. Yeah, Joel, I love that answer. I think capacity
EDDIE REYNOLDSplanning is such a critical piece of this. And you talk about like sort of going from one model to another model, back to the model. Like when you take the extreme example of Salesforce, they have such a large volume that it's really easy to say, okay, well, we need, you know, an account executive can handle this many accounts and a renewals manager can handle a lot more because renewals are just not as much work as, as managing an account and they only come up once a year. But when you're a startup, you're kind of fluctuating back and forth between these two things, because a lot of times you don't necessarily have, you know, 40 hours of work for a given task. No, usually the renewal manager
JOEL ARNOLDdoesn't have a lot of work or a renewal is an easier proposition. I have worked in one industry
JOEL ARNOLDwhere basically the renewal is a resell every time just because of the market dynamics. And, you know, we had the company that I was at was not the major player in the space. And so there was a lot of pressure to, and, and the customers were much larger organizations. Think of like a Walmart or a
JOEL ARNOLDmajor retailer, a Macy's or a Kroger. And this company was basically a startup and they, the Walmarts of the world definitely use a lot of pressure to like renegotiate and get price discounts every single year. And they won't line up with a, you know, a typical SaaS contract. So it really does depend on business.
JOEL ARNOLDBut I think the key thing there is what you pointed out is understanding the capacity of these different roles. And that's really, that's really in a lot, in many ways, what's going to determine the size of
JOEL ARNOLDthe territories that you have for CSMs or account managers or salespeople. So you definitely need to understand that. And you can't just say, well, our CSMs are going to do sales and we're just
JOEL ARNOLDgoing to hire these hybrid people because you're asking one, one person to do two very different roles, but then also maybe you need more CSMs and you don't need as many salespeople or vice versa.
JOEL ARNOLDAnd so delineating those two things is really important.
SPEAKER_84Yeah. A hundred percent. Well, this has been great, Joel. We might wrap a little early,
SPEAKER_00unless you've got anything else you want to go through. No, no. I'm excited about round two of this when we get into Eddie's best practices. Just for those
JOEL ARNOLDthat are listening, Eddie's got a lot of experience in actually doing the job of selling into existing customers for Salesforce and others. So I'm excited to hear what he's got for next week.
EDDIE REYNOLDSYeah, absolutely. And so if you guys want to see more, Joel wrote this all up in a newsletter, which we're going to publish on Friday. As I said, we'll put this out tomorrow on our podcast, which you can find on Apple or Spotify. It's RevOps Corner. And we're always here if you guys ever want to ping us with them with questions, but thank you for joining. And thanks for putting this together, Joel. Yeah. Thanks everybody.
