About this episode
Eddie Reynolds, founder and CEO of Union Square Consulting, shares his proven playbook for generating expansion pipeline in B2B SaaS companies, a process he refined during his time at Salesforce where he doubled customer spending within the first 12 months. The episode opens with a real-world example: an account manager from a large software vendor called Eddie about an upcoming renewal but missed the opportunity to discuss expansion products or upgrades, placing the burden entirely on the customer to identify opportunities. This missed interaction inspired the episode and illustrates the core operational breakdown in expansion selling.
The core thesis is simple: Expansion pipeline generation requires foundational operations (ICP and buyer personas), healthy customer identification, strategic segmentation, and bringing a unique point of view backed by research to each conversation. Rather than generic renewal calls, Reynolds advocates for account executives to research the account, understand the prospect's priorities by role and industry, and propose specific, credible expansion ideas that save the customer money or solve real problems. This reframe shifts expansion from a transactional request to a consultative discovery process that opens doors.
Reynolds breaks down the specific playbook he used at Salesforce: identify healthy customers (those actually using the product), segment by industry and role, research their business situation using public data (funding, headcount growth, competitive tools), and approach them with a hypothesis around cost reduction or coverage gaps. He illustrates this with a CFO example, showing how framing an expansion conversation around per-license discounts and bulk pricing can unlock wall-to-wall discovery across the organization. The episode covers the revenue efficiency pyramid, usage metrics, segmentation tactics, and tactical research methods that operationalize expansion at scale.
What we cover in this episode
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0:29
Generating Expansion Opportunities Introduction to operationalizing the expansion pipeline generation process and its impact on customer ARR growth.
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1:12
Missed Opportunities in Account Management Real-world example of an AE failing to explore expansion possibilities during a renewal call and lacking customer knowledge.
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3:27
Fundamentals of Expansion Pipeline How ICP, buyer personas, sales handoff, and onboarding form the foundation for successful customer expansion.
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6:08
Identifying Healthy Customers Using usage metrics and risk signals to filter accounts for expansion, focusing effort on engaged customers with growth potential.
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7:01
Segmenting Customers for Success Narrowing expansion focus by industry and role to form relevant points of view and bring credible ideas to stakeholders.
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9:19
Research and Forming a Point of View Deep-diving account research using public data, websites, and Crunchbase to develop hypotheses and unlock expansion conversations.
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11:48
Setting Up for Success Operationalizing expansion within your CRM to surface healthy customers, segment them, and enable reps to act on research insights.
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13:15
Conclusion and Next Steps Summary and invitation to explore the revenue efficiency pyramid or book a call with Union Square Consulting for expansion strategy guidance.
The lines worth sharing
An AE calling and asking if you need anything without having a point of view puts the burden on the customer to propose expansion.
Eddie Reynolds · 2:00
It's really hard to expand customers if you're not landing the right customers in the first place. If you're selling to the wrong companies, you make it harder for your AMs to expand.
Eddie Reynolds · 4:15
Instead of reaching out and asking for a QBR or renewal check-in, bring a unique point of view backed by research on the account.
Eddie Reynolds · 9:30
When I asked CFOs would you like to spend less money on your licenses with Salesforce, I can't think of a single one that said no.
Eddie Reynolds · 10:30
Common questions from this episode
How do you generate more expansion pipeline in SaaS?
Start with healthy customers (those actively using your product), segment them by industry and role, research their business situation and competitive tools, then reach out with a specific, credible point of view that solves a real problem or reduces costs, rather than generic renewal check-ins.
What fundamentals do you need for expansion selling?
Correct ICP and buyer personas, strong sales-to-onboarding handoff, solid onboarding process, usage metrics and risk signals, and the ability to segment customers by health, industry, and role within your CRM system.
How do you identify which customers to focus expansion on?
Filter for healthy customers (active users with high engagement), segment by how fast they are growing, check if they have raised recent funding, and confirm they have not yet bought all available products. About 50% of customers may not be healthy expansion targets.
What approach works best when expanding a CFO relationship?
Research the company's headcount growth, funding, and their current Salesforce license usage. Open with a hypothesis around cost reduction or bulk pricing discounts, then ask permission to run discovery across multiple departments to identify competitive tool replacement and optimization opportunities.
Why is bringing a point of view important in expansion outreach?
Without a unique perspective, you place the burden on busy buyers to self-identify expansion needs. A well-researched point of view framed around the prospect's specific priorities opens doors to discovery and consultative conversations that generic renewal calls cannot achieve.
SEO meta description
Eddie Reynolds on operationalizing expansion pipeline: segment healthy customers by industry and role, research their business, bring a unique point of view to unlock expansion revenue.
Target keywords
expansion pipeline generation
account expansion strategy
SaaS expansion selling
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Eddie Reynolds
Union Square Consulting
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Read the full transcript · 14 KB
EDDIE REYNOLDSWelcome 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. All right, welcome to another episode of RevOps Corner. Today, it's just going to be me, Eddie Reynolds. I'm the founder and CEO of Union Square Consulting, if you haven't listened to this before. And in today's episode, I'm going to talk about how to generate more expansion opportunities, specifically how to operationalize your expansion pipeline generation process and how to build the fundamentals in place so that your reps or you as a rep can identify and open up more expansion opportunities in your existing accounts. This is the process that I learned as an account executive at Salesforce, which helped them to double the spend of their average customer within the first 12 months. And also helped me to work with my plus 300 customers and expand those customers by millions and millions of dollars in ARR. So I want to start by just sharing an example that inspired this podcast and also the newsletter we wrote about it. The other day, I had an account manager or AE, I don't remember which, reach out to me from one of our vendors, a very, very large software company that you would know that I'll prefer not to name here that reached out to ask me if I needed anything or wanted anything for our upcoming renewal. I said, Hey, thanks for the call. I think we're good. And then he proceeded to end the call. And I thought, what an incredible missed opportunity. And so I gave him some feedback. It was really clear that he didn't have any idea what our company did. He didn't know what I did within the organization. He just had a name on the list, pick up the phone and called me. Equally, I've gotten a lot of these automated emails asking me if we need anything for our upcoming renewal and ignoring the retention issue here. If we're an unhealthy customer and these companies are not identifying that and pulling that out, then we have a great risk of not renewing because we're being asked if we want to renew a month before the renewal. But that's a separate topic that I'm not going to go into today. What I am going to go into is this incredible missed opportunity to potentially expand my account. And so if you think about this, this particular company has dozens, if not hundreds of additional products that I'm not even aware of. In addition to that, we are not on their top tier of the product that we have today. So there could have been a significant upgrade opportunity, but the AE or the AM, by calling me and asking me if I need anything and not saying anything more, by not having a point of view, puts it on me as the customer to come up with some idea or some question as to how I might be able to expand my account. And I'm busy. Like all of you listening, we're all busy and we're not going to go and just open the kimono for no reason to say, Hey, like, let's think about any and every way that I could spend more money with you. That's just not what we're going to do as buyers. So I'm going to lay out the process that I learned at Salesforce to help open up these conversations and generate more expansion pipeline opportunities. As this was a major focus of my role at Salesforce and a major focus for Salesforce overall in expanding their existing customers and maximizing their overall revenue growth. So let's start with getting the fundamentals in place. If you follow our content, you may have seen our revenue efficiency pyramid where we break down the four different levels of the pyramid to go from the very basics or the fundamentals all the way to the top of these shiny objects that we all get excited about, like artificial intelligence, automation, et cetera, and try to lay out a framework so companies can think about their outbound, their inbound, their sales process, and now their retention and expansion process at a fundamental level. So the fundamentals in our revenue efficiency pyramid for retention and expansion, like everywhere else, would start with the ICP and the buyer personas. And then from there going into the sales handoff and the onboarding process. Where we're going with this is it's really hard to expand customers if you're not landing the right customers in the first place. If you are selling to the wrong companies, by definition, you're going to make it really difficult for your account managers, your CSMs, your AEs to expand those accounts. If you're not engaged with the right buyer personas, or you don't know who those buyer personas are, it's going to make it more difficult to execute this process that I'm going to lay out here. And this is something that Salesforce had very, very established when I came in the door. That being said, they also didn't have it so established because we were at $5 billion in revenue when I joined Salesforce. Pretty big organization. If we're talking about a $50 million company, we really want to scale that down and sell to the right companies and not try to be all things to all people like Salesforce is today because it's just going to be too difficult for our reps to really know their customer and bring a unique point of view. So we're talking about the fundamentals here, getting the right ICP and buyer personas. We're talking about having a strong process to hand off new customers from sales to onboarding, to CSMs, to implementation, what have you, and having a really strong onboarding and implementation process. This should be well-documented. Your company should know exactly what needs to be done when, and it should be tracked in some kind of a system so that we can see that every new customer is following this onboarding process that maximizes their chance of being a healthy customer. I won't go into too much detail on this right now because it's a separate topic, but we obviously can't expand customers if they're not happy with us in the first place, if they're not using the tools. From there, we need to outline our process to retain customers and then our process to identify these expansion opportunities and sell these expansion opportunities, which I'll go into in a moment. In addition to this, it's really helpful that we start tracking usage metrics and risk signals so that we can identify which customers are healthy and which ones aren't. And that's our next step here, identifying the healthy customers. Obviously, it's pretty difficult to expand unhealthy customers. So if you're an AE or an AM and you're doing an expansion sales call down, start with healthy customers. When I was at Salesforce, unfortunately, it was about 50-50 for me. Of my 300-plus customers that I covered in the three years that I was there, about 50% of them were not healthy. They weren't using Salesforce. I mean, obviously, it's sales teams that primarily use Salesforce over all of the departments. Those sales reps weren't really logging in. I could see in the data that they didn't have a lot of records in Salesforce and weren't really using it. That's a separate conversation that I could have to try to turn that account around. But in terms of immediate payoff, there's really limited opportunity to expand those kind of accounts. So I filter out that 50% and I set my tier 1s and my tier 2 accounts to be these accounts that are healthy and have room to grow, that haven't bought every product that we have yet. And so from there, I want to segment my customers by industry or company type and by the type or sorry, and by the role. So thinking about this, I had the disadvantage of covering almost every industry at Salesforce. However, a large number of my customers and a large number of my best customers were B2B SaaS companies, especially high growth VC and PE backed like those we serve to this day. Excuse me. Got a sneeze coming on. And then the second group would have been professional services. And so if you think about trying to be all things to all people and covering every single industry, that's really difficult. If I think specifically about what a B2B SaaS company needs, it's a lot easier for me to form a point of view and bring ideas and bring relevant questions. And I have been doing this for over 10 years and still every single day, I am constantly confronted with new things about how B2B SaaS works that I don't understand. Same with professional services. I run a professional services organization and I still have so much to learn. So those two industries alone, just focusing on that is hard enough. Then we need to narrow into the role. When I worked at Salesforce, I obviously sold to VPs of sales and CROs. I also sold to CMOs because Salesforce has a lot of marketing tools. You'd think I would sell to heads of service. But what we found is oftentimes that the COO was the best person to go to for issues related to customer success and customer service. I also had a strong relationship with CFOs, the people ultimately making the decisions on what is approved for budget and not. And then, of course, the CEOs themselves. And so I'll use CFOs of B2B SaaS companies as an example in this episode to just kind of like drill in and go deeper on exactly what I was doing and the playbook that I learned at Salesforce and that I see with some of our best customers today. First, we've got to think about what do these B2B SaaS CFOs care about? They care about minimizing costs. They care about getting visibility in their forecast. And overall, they obviously care about maximizing revenue growth and the enterprise value of the organization. And so let's just kind of take the easiest one here, minimizing costs. I would want to go into my next step here, which is to do research and form a point of view. So instead of reaching out to a CFO and saying, hey, you have an upcoming renewal, or I'd like to do a QBR with you, or we haven't talked in a while, what's going on, I want to bring a unique point of view. And to do that, I need to do some research on the account. So I'm first going to look at the company website. I'm going to figure out what's going on with the company, what specifically they do, what their software does. And then I want to look for things like headcount growth. Is the company growing rapidly? Did they recently raise funding? What's going on with the organization? And how does that compare to their usage of the licenses that they've already bought from us? If they're using all of their licenses, and their headcount is growing like crazy, and it's only their sales team that's using Salesforce, then I can form a few different ideas here. Number one, they're probably going to want to buy more licenses over the coming year. So simple question for the CFO. Hey, Mr. or Ms. CFO, would you like to spend less money on your licenses with Salesforce? Of all the people I asked that question, I can't think of a single one that said no to that. So you take that and leverage that to open up some discovery. And we would explain, well, as you renew your contract with Salesforce, there's a few levers that you can pull in order to reduce your spend on a per license basis. Obviously, the more licenses you have, the deeper discounts I can provide. The more other products you have, the deeper discounts I can provide. The longer term contract you do, the deeper discounts I can provide. Could I have your permission to do some discovery with you and some of your colleagues to figure out what you're using Salesforce for today, what your needs might be, what you might need to use it for next year. And also maybe look at some of the products that you're using with some of our competitors to see if we might be able to replace those products, provide a better integration, and provide you better bulk pricing. Is that something that you would be interested in? Now, obviously, not every CFO is going to say yes to an ask that big, but many did. And this would open up a wall-to-wall discovery where I could go to the CMO, and instead of asking to do discovery with a person in a department that we have no relationship with, I'm getting the blessing of the CFO who is saying, we have an upcoming renewal, and we need you to take a look at this and compare HubSpot or Marketo, whatever you're using, to Salesforce, Pardot, which is what I was selling at the time, because this might affect our renewal. Now, obviously, this is the ideal outcome. It didn't always work that way. But this was a play that worked really well for me. And so the point I'm trying to make is that we want to set our account executives and account managers up for success so that they can actually segment their list of customers by, A, are they healthy, B, what industry or what type of company they're in. And by that, I mean, you know, it was really easy for me to say B2B SaaS companies. In other organizations, maybe it doesn't matter so much what industry you sell to. Maybe there's something else that really changes the problems that you solve for that type of company. And then thirdly, of course, is the role. And so as I go to the CFO, I'm looking to do research and to go to the website, go to publicly available information, go to Crunchbase, et cetera, and see how fast this company is growing, what funding they've raised, et cetera, that's relevant for a CFO. As I pivot and I go to a CRO or VP of sales, or then to a CMO or to a COO, or the CEO, they've got different priorities and that's going to affect the way that I do research differently, of course. And so by having this all buttoned up inside of your system, let's say that you're using Salesforce to manage your existing customers and giving your reps the ability to see which customers are healthy, to then segment that down by an industry and by particular roles, and then call down or email down on that list after having done research and bringing unique point of view can really open up the expansion opportunities for your organization. If you'd like to see more, you can check out our revenue efficiency pyramid on our website. The link will be here in the show notes. And you can see more details on all the nuts and bolts that we've laid out to really optimize your retention and expansion engine, or you could go to our website and book a call with me and we could talk through your expansion process and help identify ways to operationalize expansion and make it easier for your team to identify and open up expansion opportunities. Hope you enjoyed this episode. Thanks for listening.
