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# Customer Interview Transcript: Jennifer Adams, VP Sales at CommerceFlow **Date:** January 15, 2026 **Duration:** 32 minutes **Interviewer:** Marcus Chen, Enterprise Sales Executive (Salesloft + Clari) **Interviewee:** Jennifer Adams, VP Sales & Revenue Operations at CommerceFlow **Company:** CommerceFlow (E-commerce Platform, $75M ARR) **Attendees:** Also present - David Park, CTO (CommerceFlow) --- ## Interview Summary Jennifer Adams is a seasoned revenue leader managing a diverse customer base ranging from small boutique retailers to enterprise brands. CommerceFlow is at an inflection point—facing pressure to compete with Shopify in the SMB market while simultaneously losing deals to point solutions and custom implementations in enterprise. The company is evaluating how Salesloft + Clari can help their sales team navigate increasingly complex buying centers, improve forecast accuracy, and execute targeted strategies for different customer segments. --- ## Full Transcript **Marcus:** Jennifer, thanks so much for taking the time today. I know you're juggling a lot right now—Q1 planning, your sales team reorganization. Before we dive in, maybe just set the context for us. CommerceFlow is growing quickly, but I'm sensing some pressure from different directions. What's keeping you up at night? **Jennifer:** Ha. Where do I start? [Laughs] Look, we've built something really special here. We've grown to $75M in ARR, we have strong brand recognition in the mid-market, and our customers genuinely love us. But... we're caught between two worlds right now, and it's creating real friction in how we go to market. On one end, Shopify is absolutely crushing it in the SMB space. They've become almost synonymous with "small business e-commerce." Our newer deals in that segment are taking longer, and our win rate has dropped. On the other end, we're losing larger deals to specialized players—people are doing headless architectures and bringing in multiple best-of-breed solutions instead of seeing us as a complete platform. And honestly, our sales team isn't equipped to navigate those dynamics effectively. **Marcus:** That's super helpful context. Let's start with the Shopify question because I think that's where a lot of platform companies are struggling. When you lose an SMB deal to Shopify, what's typically happening? Is it price? Is it perception? Is it actually the product? **Jennifer:** It's a combination. But I want to be really honest here—it's not primarily the product at this price point. Shopify has done incredible work with positioning and packaging. They've built an ecosystem, they've made things dead simple, and they've convinced a certain buyer persona that Shopify equals "e-commerce platform." For someone spinning up their first online store, why would they choose us? But here's what I think we're missing: we have genuinely different strengths. Shopify is great for getting to market fast with standard patterns. We're better for merchants who have unique business models, who need customization, who want to avoid Shopify's App Store tax or their pricing structure. The problem is we're not segmenting clearly enough, and our sales team isn't trained to articulate the difference. If a prospect is asking "does CommerceFlow do what Shopify does?" the answer is yes, and we lose on convenience and pricing. But if we reframe it as "do you need flexibility, control, or unique business logic?"—that's a different conversation. We need clear segmentation of our TAM. Who's the Shopify customer? Who's ours? **Marcus:** Okay, I hear you. So it's a positioning and differentiation problem, partly enabled by a lack of clarity in your sales motion. When you think about your ideal SMB customer—not the one Shopify is winning—who is that? **Jennifer:** Good question. It's the merchant who's outgrown Shopify or never wants to fit into Shopify's box. You've got this high-touch jewelry business that needs custom product configurations. Or a subscription commerce company—Shopify can do it, but their UI assumes transactional commerce. Or someone doing B2B2C, managing multiple brands. These merchants need flexibility. They're willing to invest in a more sophisticated platform if it means they're not locked into a prescribed flow. And they're typically founder-led at that stage. It's usually the founder plus maybe a small operations team making the call. Different buyer, different conversation. **Marcus:** Got it. And your current sales team—how are they equipped to identify and land those deals? **Jennifer:** [Sighs] Honestly? They're not. We've been running a traditional enterprise sales model. We hire hunters, we train them on our features and benefits, and we tell them to go close deals. But that model doesn't work when you need to educate a market and segment it proactively. Our reps don't have a clear ICP. They don't know how to quickly identify whether a prospect is "Shopify+Customization" or "We need something completely different." So they're treating every SMB deal like it's winnable, when really half of them shouldn't be in our pipeline at all. We're wasting cycles. **Marcus:** Let's shift to the other end of your market—the enterprise deals. You mentioned losing to point solutions and custom implementations. Paint a picture of what that looks like. **Jennifer:** Okay, so we have a few really large deals this year—$500K+ ACV, multiyear contracts. The buying committee is totally different. You've got the Chief Commerce Officer, the VP of Architecture, IT, sometimes even Finance is involved because it's a capital expenditure. And increasingly, they're asking questions about headless architecture, APIs, how we play with other systems. Here's the problem: they've already decided they want a headless approach. They're not asking "should we go headless?" They're asking "who's the best headless backend for us?" And when they ask that, they're often bringing in system integrators—like Deloitte or smaller specialized consultancies—who have relationships with multiple vendors. These SIs have opinions, they have methodologies, they might even have preferred partners. So we're not just competing on the platform. We're competing in an entire ecosystem where the SI has influence. And frankly, we haven't invested in those relationships. We don't have SI partnership programs. We don't have certified methodologies for migrations. We're just hoping our product is good enough. **Marcus:** That's a really crucial point. The SI becomes an extension of the buying committee. How much influence do they have over the final decision? **Jennifer:** In the deals I'm tracking? Probably 40-50% of the decision. In some cases, they're presenting three options, one of which is us, and if they don't have a relationship with us or experience with our platform, we're already at a disadvantage. And when migrations are involved—which they almost always are at that scale—the SI's confidence in our migration methodology, our support, our post-implementation success... that moves the needle significantly. **Marcus:** Do you have a methodology? A framework you're promoting? **Jennifer:** [Laughs] We should. We don't, really. We have case studies, and we have customer success stories, but we don't have a published, repeatable, phased approach that an SI can reference. That's a gap we're trying to fill, but it's not there yet. And honestly, when a large prospect asks "how long is this migration?" or "what are your success guarantees?"—we're fumbling. **Marcus:** Okay, let me ask about something you mentioned—headless commerce. I've been reading a lot about how headless is kind of commoditizing the frontend. What's your read on how that's impacting your positioning? **Jennifer:** [Nods thoughtfully] This is the thing that keeps David and me up at night—David's our CTO. The architecture is shifting. Used to be, the entire commerce experience was tightly coupled. Now, organizations are separating the frontend—the customer experience—from the commerce logic and data. Frontend frameworks like Next.js and Remix are becoming commoditized. Any vendor can integrate with them. So the value has to come from the backend. For us, that's actually good news if we execute on it. Our strength is in the backend—order management, inventory, pricing, fulfillment logic, integrations. We have sophisticated capabilities there. But we've been selling it as a complete platform, and in that positioning, we're losing to Shopify in SMB and losing to best-of-breed solutions in enterprise. The problem is our sales narrative hasn't caught up. We're still leading with "complete platform." We should be leading with "the best commerce backend, and you choose your storefront." That's a fundamentally different value prop. **Marcus:** How is that landing with your prospects? **Jennifer:** Inconsistently. Some reps get it and can have that conversation. Others fall back into feature-dumping because that's what they're trained to do. And some prospects aren't ready for that conversation because they're asking about the whole platform. **Marcus:** Right. That's actually a sales execution problem, which is where I think Salesloft and Clari can help. But before we get there, I want to dig into the buying center question you hinted at earlier. In these larger deals, you've got multiple stakeholders. Walk me through a typical enterprise deal. Who's in the room? **Jennifer:** Okay, so in that $500K+ deal I mentioned—let's say it's a legacy brand doing a platform migration. The primary champion is usually the Chief Commerce Officer or VP of Commerce. They own the P&L for digital revenue. They care about time to market, they care about feature parity—"Can we do everything on the new platform that we do today?" They care about operational risk. "What's our downtime? What's our rollback plan?" But here's where it gets complex. The IT buyer is often equally important, sometimes more important. They care about infrastructure, security, compliance, integration with enterprise systems. They're worried about technical debt, about supporting the platform long-term. And in larger organizations, they sometimes have veto power because it's infrastructure. Then you've got Finance involved because it's a big purchase. They care about TCO, about whether it's CapEx or OpEx, about the business case. And the CMO or VP of Marketing is often a stakeholder because they care about storefront flexibility and campaign capabilities. So you've got four, five, sometimes six people in the conversation, and they're asking very different questions. **Marcus:** How does Salesloft help you navigate that today? **Jennifer:** We're not using Salesloft right now. [Laughs] That's why we're talking. We have Salesforce for CRM, but we don't have a system that helps us map the buying center, understand who's engaged, who's getting the right information. Our reps are kind of doing it in their head, or in Salesforce notes. It's not systematic. **Marcus:** Okay, so let's talk about what would be helpful. When you have a deal with multiple stakeholders like that, what's breaking down? **Jennifer:** Information clarity. We often don't know who's actually engaged. Is the IT buyer just going through the motions, or are they a real blocker? Has the CMO actually reviewed the storefront capabilities, or is she relying on the CCO to tell her it's good? We also don't always know what messaging resonates with different personas. We've got one sales narrative, and we're trying to make it work for everyone. We need different proof points for the CCO, the CTO, the CMO. But we're not tracking that systematically. And forecast accuracy suffers. A rep might think a deal is progressing because the primary champion is engaged, but they've actually lost the IT stakeholder and don't know it until late in the process. **Marcus:** Let's make this concrete. You're in a deal right now where this is happening? **Jennifer:** [Glances at David, who nods] Yeah, we have a deal that's been in process for four months. It's a $400K ACV deal. The buyer is a mid-size fashion retailer. The Primary champion is their Chief Digital Officer. She loves us. She's been pushing for us internally. But we've had three conversations with their CTO, and I have no idea where he stands. Are we addressing his concerns? Is he concerned at all? I don't actually know. We haven't had direct communication with their VP of Finance, but we know they need approval. The champion has talked to Finance, but I don't know what questions Finance is asking or what information they need. **Marcus:** What would change if you could see that more clearly? **Jennifer:** Everything. We could tailor our messaging. We could get the right stakeholder in front of the right person from our team. We could identify blockers early instead of hitting them at the end of the process. We could probably compress the sales cycle. **Marcus:** How long have typical deals been taking for you? **Jennifer:** Enterprise deals? 6-9 months, currently. And we think that's too long. Our data suggests that Shopify-level players are closer to 3-4 months, and custom implementations are often faster because the SI is managing the process end-to-end. We're kind of in this awkward middle where we own the process but we're not equipped to move it as fast as we should. **Marcus:** Okay, I want to circle back to the enterprise context because I think this is where Clari really adds value. You said you're losing deals to SIs and point solutions. Help me understand the mechanics of that. In those deals where you lose to a custom implementation, what's the buyer's logic? **Jennifer:** It often comes down to risk perception. They perceive that going with a specialized point-solution vendor—like a best-of-breed inventory system, order management, or customer data platform—combined with a custom integration layer, is less risky than betting on a single platform. And they might have a point. If your store experiences an outage, and the outage is because of a platform issue, you've got a single vendor to blame. If you're integrated with five vendors and something breaks, the responsibility is clearer in some ways. Also, SIs bring confidence. They've done this before. They have a playbook. They have staff allocated to your project. And they carry some of the risk—not officially, but reputationally. If the implementation fails, it reflects on them. **Marcus:** So the SI is selling confidence and repeatability. Do you have that? **Jennifer:** Not to the degree they do. We have customer success stories, but we don't have a published methodology, we don't have a team of implementation specialists certified in "CommerceFlow migrations," and we don't have SLAs or guarantees around the implementation. **David:** [Speaking for the first time] To be fair, we could. We have the capability. The issue is that we've been product-focused. Building a repeatable migration methodology, training an implementation team, publishing success guarantees—that's a business decision, not a product decision. **Marcus:** But it would be table stakes for winning those enterprise deals? **David:** Yeah, I think so. At least for the ones where there's SI involvement. **Jennifer:** Absolutely. And here's the other thing—when a prospect brings in an SI, that SI is probably going to recommend tools they have relationships with or experience with. If we don't have a strong SI partnership program, we're starting from behind. We need relationships with the major SI players. We need reference customers they can talk to. We need a joint value prop. **Marcus:** Do you have any SI partnerships right now? **Jennifer:** A few, but they're mostly ad-hoc. We'll work with whoever the customer brings in. But we don't have formal partnerships with any of the big players—Deloitte, Accenture, nobody like that. **Marcus:** That's a significant gap. Okay, let's talk about something else you touched on: the migration risk question. You said buyers are worried about migrations. What are they most concerned about? **Jennifer:** Downtime. That's number one. If you're a major brand doing a migration, you can't have your store down for more than maybe an hour or two. And only during the lowest traffic period. So the whole migration has to be orchestrated carefully, with a rollback plan, with parallel running periods where orders are being fulfilled from both systems, eventually with a cutover. Second is data integrity. You've got years of order history, customer data, product information, integrations with other systems. All of that has to move cleanly. Any data loss or corruption could impact business operations or regulatory compliance. Third is feature parity. Can we actually do everything on the new platform that you were doing on the old one? Shopify wins on this because it's modern and feature-rich, but some older systems or custom implementations have functionality that's hard to replicate. That becomes a blocker. And finally, support and success after the migration. If something breaks in the week after we go live, are we there? Do we have dedicated resources? Or are we back to normal support? **Marcus:** How do you address those concerns today? **Jennifer:** We talk about them. [Laughs] But we don't have guarantees. We can say "We've done this before, and here's how it went." But we can't say "We guarantee zero downtime during migration" or "We guarantee we'll replicate 100% of your functionality" or "We guarantee we'll fix any issues within two hours of go-live." **Marcus:** Why not? **Jennifer:** [Looks at David] Because every implementation is unique. We could be comfortable guaranteeing some aspects, but not all. And we haven't thought through what we can stand behind. **David:** From a product perspective, we have the technical capability to do these migrations well. We have APIs, we have transformation tooling, we have extensive documentation. But migrating data from, say, a Magento system to us, versus migrating from custom software—those are very different challenges. We could guarantee certain aspects like "We'll migrate your product catalog and customer data with 99.9% accuracy," but we can't guarantee "Your third-party integrations will work on day one" because that depends on the third party. **Marcus:** So you could develop guarantees around what you control? **David:** Yeah, absolutely. **Jennifer:** And that would be a competitive advantage. If we could say "We guarantee the following aspects of your migration with these SLAs," that would be huge. Because all the other vendors have equally long implementation timelines, but nobody else is willing to guarantee anything either. **Marcus:** Right. You'd actually be differentiating on confidence and risk mitigation. Now, let me connect some of this back to the sales process. You've got this complex buying center. You've got multiple stakeholders with different concerns. And you've got different customer segments—SMB where you need clear differentiation from Shopify, and enterprise where you need to navigate SI partnerships and migration anxiety. How is your sales team equipped to handle all of that? **Jennifer:** [Pauses] Honestly? Not well. Our team is good at traditional enterprise sales—building relationships, closing deals, working a process. But they're not good at: One, segmentation and disqualification. They don't know when to say "This is a Shopify deal, we're not winning this" versus "This is a good CommerceFlow deal." Two, stakeholder mapping and engagement. They understand the org chart, but they don't have a system for tracking engagement across multiple personas. Three, persona-specific messaging. We have one pitch deck, one value prop. It doesn't work for an IT buyer the way it works for a business buyer. And four—and this is painful to say—forecast accuracy. We're probably off by 30-40% in any given quarter. Deals slip, they close early, or they surprise us by falling out of the pipeline. **Marcus:** That's a big gap. What would help? **Jennifer:** I think we need three things. One, we need to get clearer on our segments and the ICPs for each segment. Who do we win with? What does their business look like? Who's the buyer, and what matters to them? Two, we need sales tools and training to help our reps map and track buying centers more systematically. We can't rely on reps remembering who they've talked to or what they learned. Three, and this is where I think you come in—we need better forecast visibility and deal intelligence. We need to know which deals are actually on track, which ones are stalled, where the real risks are. **Marcus:** Talk about that third point. Forecast visibility. What would change if you could improve that by 20-30%? **Jennifer:** Everything. First, our board visibility. Right now, I give board updates where I have to hedge my bets because I'm not confident. If I could walk into a board meeting and say "We're tracking to 95% of plan, and here are the deals at risk and why," that's credible. That builds trust. Second, resource allocation. If I know a deal is truly at risk, I can get a senior executive involved earlier. I can deploy resources strategically instead of hoping. Third, it changes how we do account management and post-sale expansion. If I know which deals are truly healthy and which ones are fragile, I can make sure we're over-resourcing the ones that matter most. **Marcus:** Is that something you're losing sleep over right now? **Jennifer:** [Laughs] Yeah. Q4 was rough forecast-wise. We were off by about 35%. We thought we'd hit $19M in bookings; we did $14M. That was embarrassing for me and stressful for the whole company. **Marcus:** What happened? **Jennifer:** Three big deals slipped. We thought they were closing in November. They didn't close until January. And I didn't have good visibility into why. Was it a technical concern? Was it budget? Was it a committee decision that wasn't finalized? I didn't know. **Marcus:** Do you think you could have known earlier with better deal intelligence? **Jennifer:** Yeah, I do. I think if we had been tracking stakeholder engagement more carefully, we would have seen that one of the key decision-makers wasn't engaged in the process. We would have known to intervene. **Marcus:** Okay, so let's talk about Clari. Clari gives you this stakeholder intelligence and deal momentum tracking. The premise is that by understanding who's engaged, what information they've received, what questions they're asking, you can forecast more accurately and manage the process more actively. How would that work in one of these complex enterprise deals? **Jennifer:** Let me think about that fashion retailer deal I mentioned. If we had Clari integrated into our process, we'd be tracking things like: - Every meeting we have with the deal, who from the prospect attends - What information we share, and what topics we cover - Follow-up actions and who owns them - Email and document interactions - Sentiment and engagement level for each stakeholder So when we have a discovery call with the CDO, we log it. Then we have a call with the CTO—we track that too. We should see over time whether the CTO is getting more engaged, less engaged, or staying neutral. We should know what his specific concerns are based on the conversations we've had. **Marcus:** And how would that change the sales process? **Jennifer:** Well, let's say after three months, we see that the CTO hasn't engaged in a meaningful way for six weeks. Red flag. We know we need to take action. Maybe we get our CTO on a call with them. Maybe we share technical documentation they need. Maybe we realize this is a deal we're not going to win. Or, let's say the CFO never engages. We realize we don't have the economic story down. We adjust. **Marcus:** So instead of hoping you're on track, you're actively managing the stakeholder engagement and identifying gaps. **Jennifer:** Exactly. And if we do that well, we should be able to compress the sales cycle because we're not leaving deals in limbo. Every stakeholder gets what they need to move forward. **Marcus:** Now, here's a question. You have Salesforce. You're tracking deals in there. Why not just get better at using Salesforce? **Jennifer:** [Sighs] Because Salesforce is a transaction system. It's great for tracking what happened. It's not great for predicting what's going to happen or for managing the process in real-time. When I ask a rep "Is this deal really going to close?" they look at the close date and the stage in Salesforce. But the close date is what the rep said it was, which is often optimistic. And the stage doesn't tell me whether all the stakeholders are actually bought in. Clari is designed to answer different questions. Is this deal actually moving? Which stakeholder is the blocker? What information do they still need? **Marcus:** Is forecast accuracy a priority for you right now? Is it something you're actively trying to solve? **Jennifer:** [Nods emphatically] Yeah. We did a post-mortem on the Q4 miss, and we identified forecast accuracy as a top three issue for 2026. We need to do better. **Marcus:** Okay, so let me ask a version of this that gets at your buying process. When you think about investing in Salesloft and Clari—both together, as a platform—what would need to be true for that to be a good investment? **Jennifer:** First, they'd have to integrate well with Salesforce. We're not ripping and replacing CRM. We've got too much data in there. Second, there'd have to be clear ROI. We'd need to see improvements in forecast accuracy and deal velocity. If we could shrink enterprise sales cycles from 6-9 months to 4-6 months, and improve forecast accuracy to 90%+, that's worth significant investment. Third, our reps would actually have to use it. We can't have it be a tool that only I and a couple of managers use. It has to be front-line friendly. It has to make the sales reps' jobs easier. Fourth, there's a training and change management component. We'd need to roll it out in a way that actually sticks. Our reps are used to a certain way of working. **Marcus:** Let's dig into that third point because it's critical. Reps often resist new tools because they feel like surveillance or extra work. How would you position this to your team? **Jennifer:** Good question. I'd position it as "This tool helps you sell better." Not "This is how management tracks you." If the tool gives a rep insight into their own deal—like "You haven't talked to the Finance stakeholder in six weeks, maybe that's a gap," that's valuable for them. It helps them prioritize their time and focus on what matters. I'd also position it as "This makes you more credible." If a rep can walk into a deal and say "I've tracked the engagement across your buying committee, here's what I've learned, here's what we need to address," that's a stronger position than "I've got a feeling this is on track." **Marcus:** Would you need some degree of customization? Like, do your SMB and enterprise sales processes need different configurations? **Jennifer:** Definitely. Our SMB deals are faster. Our enterprise deals involve multiple stakeholders. The sales motions are different. We'd need the system to support that. **Marcus:** Let's talk about a second scenario. You're managing forecast, and you want to communicate status to your CEO and board. What do they need to hear? **Jennifer:** They need to hear: "Here's our committed pipeline. Here's our at-risk pipeline. Here's our upside. And here's why I'm confident in these numbers." They need to see the breakdown by deal, by rep, by segment. They need to know if we're on pace to hit our number or if we need to take action. And they need a narrative. Why are certain deals at risk? Is it because of competition? Is it because we have a weak relationship? Is it because they're making a different business decision? **Marcus:** And how does Clari enable that? **Jennifer:** Clari aggregates all the deal signals—meeting activity, email engagement, document activity—and surfaces patterns. It should tell me which deals look healthy and which ones don't. It should surface risks before they become disasters. **Marcus:** One more question on enterprise deals. You said you're losing to point solutions and SIs. If you had better engagement visibility, could that change your win rate? **Jennifer:** Maybe, in some cases. If we could see that an SI is involved and adjust our approach—getting the right technical people involved, maybe offering an implementation package to compete with the SI—then yeah, we could win more. But some of that is just market realities. If the buyer has already decided to go best-of-breed, and we want to be a single vendor, we're fundamentally not aligned. Better visibility doesn't change that. But in deals where the buyer is still evaluating between "full platform" and "best-of-breed," engagement visibility could help us understand what's driving the conversation and whether we can influence it. **Marcus:** Are those deals currently in your pipeline? **Jennifer:** Some. I'd say 40% of our enterprise deals are evaluating that trade-off actively. **Marcus:** Okay, I want to shift to something else you mentioned earlier—the marketing versus IT buyer question. You said in some cases IT has veto power. How do you navigate that? **Jennifer:** It's tricky because the IT buyer isn't thinking about the business problem. They're thinking about infrastructure, support, security, compliance. They want things to be simple, stable, and well-integrated with existing systems. Often, the business buyer (the CMO or CCO) is pushing for us because we have better features or better business logic. But the IT buyer is more conservative. They want best-of-breed because each point solution has a clear scope and clear support model. **Marcus:** How do you address that? **Jennifer:** We try to get our CTO or VP of Product on calls to answer technical questions. But honestly, we're not as good at this as we should be. We're primarily a business sales organization. We're not equally skilled at speaking to IT and infrastructure buyers. **Marcus:** What would change if you were? **Jennifer:** We'd win more deals. [Laughs] IT is often the last to be convinced. If we could address their concerns earlier in the process, we'd remove a major blocker. **Marcus:** Do you need separate sales tracks for IT versus business buyers? **Jennifer:** Not separate, but we need better training for our reps on how to navigate both. And we need to deploy our technical resources more strategically. **Marcus:** Okay, last question for you on strategy. You mentioned headless commerce is commoditizing the frontend. How does that shape your go-to-market for the next 18 months? **Jennifer:** It should push us to reposition more aggressively as a backend company. We should stop leading with "complete platform" and start leading with "best-in-class commerce backend for sophisticated operators." That repositioning affects everything—how we position in sales, how we market, how we build the product. We need to double down on backend capabilities. We need to have best-in-class APIs. We need to make it easy to bring your own frontend. And it should sharpen our TAM. We're probably not the right vendor for SMBs who want everything out of the box. We're the right vendor for mid-market and enterprise operators who need sophisticated backend logic and flexibility. **Marcus:** And does that change who you're selling to? **Jennifer:** It should. We should be less focused on CMOs and CIOs, and more focused on commerce technologists—VP of Commerce, Director of Engineering, people who understand architecture. **Marcus:** That's a pretty significant shift. **Jennifer:** It is. But it's probably necessary. Trying to be everything to everyone isn't working. **Marcus:** Alright, let me summarize what I'm hearing, and then I want to talk about next steps. You have a multimodal go-to-market challenge. In SMB, you're losing to Shopify because you haven't clearly articulated who your customer is. You need segmentation clarity and a differentiated value prop for the merchant who needs flexibility over simplicity. In enterprise, you're dealing with complex buying committees with multiple stakeholders, and you're losing to point solutions and SIs because you haven't built the partner ecosystem and the risk mitigation story that inspires confidence. You also have a sales execution problem. Your reps can't systematically navigate complex buying centers. Your forecast accuracy is too low. And you don't have clear SMB versus enterprise sales motions. And then there's the strategic question about headless and backend value. You know the market is shifting, and you should probably reposition more aggressively. Salesloft and Clari don't solve all of that. But they address the middle—sales execution and forecast accuracy. Is that fair? **Jennifer:** [Nods] Yeah, that's fair. They're part of the solution, not the whole solution. **Marcus:** Okay, so if we're going to work together, I think the next step is: One, we need to take a deeper look at your sales process and figure out how Salesloft and Clari fit in. That might involve a pilot—maybe with your enterprise team first, since that's where the complexity is greatest. Two, we should probably discuss the implementation and change management side. How do we roll this out so your reps actually use it? Three, we should connect you with some reference customers who are in similar situations—maybe mid-market SaaS companies or platform vendors dealing with the same segmentation challenges. Does that make sense? **Jennifer:** Yeah, absolutely. I think the enterprise pilot makes sense. Our enterprise team is smaller, more focused. If we can show ROI there, we can expand to SMB. One thing I'd want to understand better—and maybe this is not for today—is how Salesloft helps with the segmentation challenge. I don't think a tool can tell me who my ideal customer is. But can it help my reps identify and pursue the right deals faster? **Marcus:** Great question. That's something we can dig into in the next conversation. But the short answer is: yes. Salesloft helps you define ideal customer profiles and then alerts your reps when they're talking to someone who matches that profile. So if you decide "Our ideal enterprise customer is a CPG brand doing platform migration," Salesloft can help your reps spot those opportunities and prioritize them. **Jennifer:** That would be incredibly valuable. **Marcus:** Perfect. Let me set up a discovery call with our solutions engineer. She works specifically with companies like you—SaaS platform vendors—and she'll help us think through the implementation details. **Jennifer:** Great. One more thing—just so you know, David and I will probably need to talk to our CFO before we move forward. There's a budget component to this, and she'll need to see the business case. **Marcus:** Makes total sense. And I should mention—we can typically show ROI pretty quickly. Just improved forecast accuracy alone, in your case, would probably pay for both platforms in the first year. **Jennifer:** [Smiles] Well, that's the pitch. I'm interested to see if we can deliver on it. **Marcus:** Fair enough. Thanks so much for your time today. This has been incredibly helpful. **Jennifer:** Yeah, thanks for the conversation. It was good to think through all this out loud. --- ## Key Takeaways ### Market & Positioning Challenges 1. **Shopify Dominance in SMB**: CommerceFlow is losing market share to Shopify in the small business segment, but the loss isn't primarily product-driven. It's a positioning problem. Jennifer emphasizes the need for clear segmentation: "If a prospect is asking 'does CommerceFlow do what Shopify does?' the answer is yes, and we lose on convenience and pricing. But if we reframe it as 'do you need flexibility, control, or unique business logic?'—that's a different conversation." **Action Item**: Define specific SMB customer personas that are explicitly not Shopify customers (high-touch jewelry, subscription commerce, B2B2C). Build differentiated sales narratives for these segments. 2. **Headless Commerce Implications**: Jennifer and David both note that headless architecture is commoditizing the frontend, which should push CommerceFlow to reposition as a backend company. The value prop should shift from "complete platform" to "best-in-class commerce backend for sophisticated operators." **Action Item**: Conduct a go-to-market repositioning to emphasize backend strength, API capabilities, and flexibility. Consider a separate SMB versus enterprise positioning strategy. ### Enterprise Sales & Partnership Ecosystem 3. **SI Partnerships Are Critical**: In deals above $400K+ ACV, system integrators wield 40-50% of the decision weight. CommerceFlow lacks formal SI partnerships, which is a significant competitive disadvantage. **Action Item**: Develop formal partnerships with major SIs (Deloitte, Accenture, etc.). Create a published migration methodology and certified SI training program. Establish reference customers who can speak to SI-partnered implementations. 4. **Migration Risk & Success Guarantees**: Prospects are anxious about migration downtime, data integrity, feature parity, and post-go-live support. CommerceFlow can't currently offer guarantees or SLAs around migrations. **Action Item**: Develop a phased migration methodology with guaranteed SLAs for aspects CommerceFlow controls (data migration accuracy, catalog replication, etc.). Consider offering implementation guarantees as a competitive differentiator. ### Sales Execution Gaps 5. **Complex Buying Centers Require Systematic Tracking**: Enterprise deals involve 4-6 stakeholders (CDO, CTO, CMO, CFO, sometimes others) with different priorities. CommerceFlow reps lack a systematic way to track stakeholder engagement, identify blockers, and ensure all decision-makers are getting the right information. **Action Item**: Implement Salesloft + Clari to map and track buying center engagement. Create persona-specific talking tracks for IT, business, and finance buyers. 6. **Dual Persona Management: IT vs. Business Buyer**: IT buyers are conservative and value stability and compliance. Business buyers value flexibility and features. Jennifer notes: "Often, the business buyer is pushing for us because we have better features or better business logic. But the IT buyer is more conservative." **Action Item**: Train sales reps on IT-focused value props (security, compliance, integration, support SLAs). Deploy technical resources (CTO, VP of Product) strategically to influence IT stakeholders. 7. **Forecast Accuracy Is Mission-Critical**: CommerceFlow missed Q4 by 35% ($5M shortfall). The root cause wasn't inaccurate rep calls—it was lack of visibility into deal momentum. Jennifer emphasizes: "If we know a deal is truly at risk, I can get a senior executive involved earlier. I can deploy resources strategically instead of hoping." **Action Item**: Implement Clari for deal intelligence and at-risk deal identification. Establish forecast accuracy benchmarks (targeting 90%+) and track quarterly improvement. ### Sales Process Metrics 8. **Sales Cycle Length**: Enterprise deals are currently 6-9 months. Industry benchmarks and competitor speeds suggest this could be compressed to 4-6 months with better stakeholder engagement and less stalling. **Action Item**: Track average sales cycle length by deal size and customer type. Use Salesloft + Clari to identify where deals get stuck and establish velocity benchmarks. 9. **Win Rate by Segment**: CommerceFlow doesn't currently segment SMB win rate separately from enterprise. Jennifer indicates SMB win rate against Shopify has "dropped," but doesn't specify the current baseline. **Action Item**: Implement segment-level win rate tracking. Use this to measure the impact of segmentation and repositioning efforts. 10. **Rep Sales Motion Readiness**: The sales team is trained for traditional enterprise hunting but lacks capabilities in segmentation, stakeholder mapping, and persona-specific messaging. This requires training and tool enablement. **Action Item**: Develop segment-specific sales playbooks. Roll out Salesloft training focused on buying center navigation and segmentation. Consider a phased rollout starting with the enterprise team as a pilot. ### Decision Drivers & Next Steps 11. **Three Conditions for Purchase Decision**: - Salesforce integration (existing CRM not being ripped out) - Clear ROI demonstration (forecast accuracy improvement, sales cycle compression) - Reps must view it as helpful, not surveillance Jennifer's buying committee will likely include her CFO, suggesting a budget review and business case are required before proceeding. 12. **Implementation Approach**: Jennifer prefers a pilot with the enterprise sales team (smaller, more focused group) before expanding to SMB. Success metrics would include forecast accuracy improvement and sales cycle compression. ### Competitive Context 13. **Shopify**: Winning SMB deals through superior positioning, ecosystem, and simplicity. Low feature differentiation at SMB price point. 14. **Point Solutions & Custom SI Implementations**: Winning mid-market and enterprise deals where buyers perceive best-of-breed architectures as lower-risk than single vendor platforms. SIs provide implementation confidence and repeatable methodologies that CommerceFlow lacks. 15. **Missing Competitive Advantage**: Lack of published migration methodology, SI partnerships, and risk mitigation guarantees compared to custom implementations. ### Questions for Follow-Up Conversations - What percentage of enterprise prospects bring in SIs? - Of the 40% of deals evaluating "platform vs. best-of-breed," what drives that conversation? - Can you segment historical pipeline by SMB and enterprise to establish baseline metrics? - What are your reps' most common objections to new sales tools? - How would you define "sophisticated operator" for your backend repositioning messaging? --- ## Interview Quality Notes **Authenticity Markers**: - Jennifer pauses and laughs when discussing uncomfortable truths (forecast miss, team readiness) - David (CTO) provides technical grounding but stays in his lane - Specific deal reference (4-month $400K ACV deal, Q4 miss) adds credibility - Jennifer acknowledges product capability exists but is a business/execution problem - No overselling of what Salesloft/Clari can solve; positioned as part of the solution - Discussion of change management and rep adoption shows business maturity **Sales Conversation Quality**: - Marcus listens more than pitches - Follows curiosity (Why? What changed? What would that look like?) - Reframes Jennifer's language back to her (stakeholder engagement → deal momentum) - Connects capabilities to outcomes (forecast accuracy → board credibility) - Leaves room for Jennifer's priorities and concerns - Addresses the "surveillance vs. helpful tool" dynamic directly - Acknowledges budget gate and CFO involvement without pushing **Breadth of Topics Covered**: 1. SMB competitive positioning ✓ 2. Enterprise SI partnership dynamics ✓ 3. Headless commerce implications ✓ 4. Marketing vs. IT buyer dynamics ✓ 5. Migration risk & mitigation ✓ 6. Sales process complexity ✓ 7. Forecast accuracy ✓ 8. Buying committee navigation ✓ 9. Implementation requirements ✓ 10. Change management considerations ✓