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# Interview: Kevin O'Brien - Dental/Specialty Practice Software CRO ## Metadata **Date:** January 2, 2026 **Duration:** 30 minutes (3,847 words) **Interviewer:** Sarah Chen, Salesloft Enterprise Solutions **Interviewee:** Kevin O'Brien, Chief Revenue Officer, Specialty Practice Software **Company:** Dental & Specialty Practice Management Platform **Company Size:** $45M ARR | 150+ employees | 8,000+ customer practices **Interview Format:** Video call (transcribed) --- ## Conversation Transcript **SARAH:** Kevin, thanks so much for taking the time. I know you're incredibly busy, especially coming off what I'm sure was a strong quarter. I'd love to understand your go-to-market challenges as you're scaling. Let's start with the most immediate thing on your plate—how are you thinking about growth right now? **KEVIN:** Yeah, honestly, Sarah, growth is exactly the problem. Sounds weird to say it that way, but we've hit this inflection point where our model is breaking. We've gone from maybe 40 reps five years ago to 150 now, and the math on acquisition isn't stacking anymore. Our ACVs are around $8K to $12K depending on practice size, and that's just... it's tight. **SARAH:** That's actually one of the things I wanted to dig into. $8K to $12K per year—that's definitely SMB territory. Walk me through how you think about lead generation and qualification with that ACV. What does your funnel look like? **KEVIN:** So the challenge is volume. You need volume. With an $8K ACV and a typical two-year ramp on commission, a rep can't afford to spend six months on one deal. We're talking about deals that close in maybe 60 to 90 days on average, with some taking longer. We've got reps who might be working 40, 50 deals in various stages. It's a high-velocity game. Lead gen is a mixed bag. We're doing Facebook ads, Google ads, some content marketing. We work with a few partners who have practice owner lists. But here's the thing—our conversion rate from initial contact to qualified opportunity is maybe 3 to 4 percent. Most practice owners get bombarded with software vendors every single day. They hear from DSOs, they hear from accounting firms, consultants. When a rep from our sales team reaches out, they're one of many. **SARAH:** And how are you qualifying within that volume? Are you using any tools or criteria to help reps figure out who's actually a fit? **KEVIN:** We try. We use a basic scoring system—practice size, revenue, region, whether they've expressed any pain around scheduling or billing. But honestly, with 100-plus thousand prospects in the addressable market, we're still trying to figure out segmentation. That's actually a big pain point for us. We have DSOs—Dental Service Organizations—that operate hundreds of locations. Those are $100K+ deals, multi-year, very structured. Then we have independent practices with 5, 6, 10 dentists that might be $10K to $15K. And we have solo practitioners that are in the $5K range. The economics are completely different for each segment. Our reps are taught to target the mid-market independents because the deal size is reasonable and the sales cycle isn't insane like with the big DSOs. But that's like... 70,000 prospects right there. How do you prioritize? **SARAH:** This is where segmentation and channel strategy becomes critical. You mentioned you have 150 reps. How are they organized? Are they geographic? Industry? Vertical? **KEVIN:** Mostly geographic. We've got territories covering metro areas and regions. But here's where it gets messy—we also have partnerships with some DSOs and larger group practices who want to white-label or integrate our solution. Those aren't really led by sales, they're kind of strategic relationships. But then you've got this overlap problem. A DSO might operate in 15 states. My reps in California are contacting solo practices in the DSO's network. The DSO wants to take the deal because they get a cut. My rep wants the deal because it's in their territory. We're stepping on our partners' toes constantly, and we're losing deals to cannibalization. **SARAH:** That's channel partner cannibalization—it's a classic problem at your scale. How is that impacting your team? What's the friction? **KEVIN:** It's costing us money and it's demoralizing for reps. We had this situation where a partner in the South had a deployment going with a 40-location DSO. My team got wind of it and started prospecting locations in that DSO independently. We're talking about maybe $4K per location times 40 locations. That's $160K in annual recurring revenue potentially, maybe $250K total contract value. The partner felt like we were undermining them. We lost the deal entirely because the DSO said, "You guys aren't coordinated. We don't know who to trust." Now the DSO is looking at a competitor. The partner wants us to sign something that gives them exclusive territory, but my head of sales said, "That's career suicide. We're not ceding a whole state to a partner." So we're stuck in this middle ground where partners are upset, reps are frustrated because they don't know what accounts they can actually touch, and we're leaking revenue out the back. **SARAH:** And with that kind of ambiguity in the market, your conversion rates are probably suffering. I want to talk about something you mentioned earlier—demo quality and conversion decline. What's happened to your demo-to-close rate over the last two years? **KEVIN:** [sighs] That's the thing that actually keeps me up at night. Two years ago, if a practice owner took a demo with us, we were closing maybe 35 to 40 percent of those. Last year, it dropped to maybe 22 percent. This year, we're tracking around 18 to 20 percent. A practice owner sees a demo, they like the product, and then... they don't buy. We used to think it was objection handling. Now I think it's something deeper. **SARAH:** What do you think changed? Product-wise, market-wise? **KEVIN:** Both. On our side, we're not differentiating anymore. Four or five competitors emerged—some homegrown, some backed by private equity. They all do roughly the same thing. A practice owner can see our demo, see theirs, and it's like, "Yeah, they're basically the same." We're commoditizing. But there's also something about the buying behavior that's changed. Practice owners are more cautious. They talk to each other. I'll have a prospect say, "Yeah, I know three practices using you. Let me call them." And I'm like, "Great, go ahead." But then they come back and say, "One of them said your onboarding was a nightmare. One said the support was slow." So suddenly the deal's at risk. Referrals used to carry a lot of weight. Now referrals with caveats are almost worse than no referral because it's like, "We like your product but..." And that "but" is hard to overcome. **SARAH:** So you're in this weird situation where product and market fit is there, but competitive noise and social proof are working against you. What's your rep quality look like? Are your reps equipped to handle that dynamic? **KEVIN:** That's maybe where I'm most frustrated. We hired aggressively over the last three years. A lot of our reps are junior. We pay okay—$50K base, $60K OTE with uncapped commission. But the truth is, onboarding a rep to handle dental practice owner psychology is not straightforward. Dental practice owners are often founders. They've built their practice from scratch. They're emotional about their business. They're not going to respond to some kid who just reads the feature sheet. They need someone who understands their pain—scheduling conflicts, staffing issues, collections problems. They need relationship selling. But when you're working 40, 50 deals at a time, you can't build relationships. You're doing discovery calls, sending demos, following up on objections. You're in a transactional mode, not a relational mode. And the owner-operators can feel it. They can feel whether you actually care about their practice or if you're just trying to hit quota. **SARAH:** That's such an important point. Let me ask this differently. When you think about the deals you're winning versus the deals you're losing, what's the difference in how the rep engaged? **KEVIN:** The reps who are winning are usually doing something different. They're asking more questions upfront. They're not jumping to the demo. They might have two or three conversations with a practice owner before that owner sees a single screen. They're uncovering the real problem. I had a rep, Jessica, who moved into our Chicago territory about eight months ago. She's mid-career, came from healthcare tech. In her first three months, she had maybe one-third the activity of the junior reps. But her conversion rate from qualified opportunity to close was like 45 percent. She was winning deals that looked dead. Practices that other reps had already talked to. How was she doing it? She was calling practice managers, office managers, not just the owner. She was understanding the workflows. She'd say something like, "I noticed you're still using paper schedules in your front desk area. That's causing this specific problem." And suddenly the owner's leaning in because she clearly knows what she's talking about. **SARAH:** So you've got Jessica who's doing it right, but you can't scale that approach with 150 reps and $8K ACVs. What do you do? **KEVIN:** Exactly. We're trying to teach it. We've got sales enablement folks writing playbooks, creating videos. But it's hard to scale one person's intuition and work ethic. And here's the thing—Jessica is probably going to get poached by a larger company or start her own thing in a year. That's the other problem with SMB sales. Your best reps burn out or move up. We're also facing this ceiling on how many reps we can deploy profitably. If a rep is producing $400K to $500K in ARR per year, and we're paying them $110K in salary and commission, that works. But if we hire another 50 reps and they produce $300K each because the market's more saturated, suddenly our unit economics are broken. **SARAH:** So you're constrained on headcount growth because the model doesn't work at scale. But you still need growth. What are you thinking about in terms of strategy? Are you looking at moving upmarket? **KEVIN:** We're exploring it. The DSO space is attractive. Some of these DSOs are massive—hundreds of locations, millions in revenue. One deal could be worth $500K in ARR. You'd only need ten of those to have a multi-million dollar year. But the sales cycle is 6, 9, sometimes 12 months. You need enterprise reps who cost more. And you're competing against massive players. We're also thinking about channel partners more strategically. Instead of this cannibalization mess, what if we really build out a partner program? We could have accountants, consultants, DSO management companies who sell through us. They take a cut, we get the volume, and it's not on our rep headcount. But that requires a completely different infrastructure. Partner enablement, partner marketing, partner support. We're not set up for that. **SARAH:** Let me ask about the owner-operator psychology piece because that feels like it's the real thing. You've mentioned that a few times. A practice owner who's built their own business from nothing is going to have different buying criteria than, say, a CFO at a DSO. What are those criteria? **KEVIN:** It's personal. For an owner-operator, the business is their baby. They've invested 15, 20, 30 years into it. They're making $200K, $300K, $500K in profit depending on the practice size. Any software change, any operational change feels risky. They also have trust issues. They've had bad experiences with software vendors. They might have paid $50K for a system five years ago that promised to integrate with everything and never worked right. So when we come in and say, "Our software will solve your staffing problems," they're thinking, "Sure, you say that, but I've heard it before." The other thing is they're often not tech-native. They're dentists first, business people second. They might have an office manager or a general manager who's more tech-forward, but the owner still has to feel comfortable. They need to see it, touch it, understand it. And there's the personal impact piece. If we implement our software and it goes badly, the owner has to manage that. If we go out of business or sunset a feature, it affects their practice. If we have a data breach, it's their practice's reputation at risk. So the switching costs aren't just the time and money to implement—they're personal and emotional. **SARAH:** That's really clear. So the owner is essentially asking, "Can I trust this company with my business?" not "Does your feature set match our requirements?" **KEVIN:** Exactly. And that's where relationship selling matters. If a rep has spent time understanding the owner's world, asking good questions, showing genuine interest in the practice, the owner is more inclined to trust them. The owner knows the rep will be there during implementation. The owner feels like they're not just a line item on a spreadsheet. But our current model doesn't support that. We're incentivizing reps to move deals through the pipeline as fast as possible. And you know what? I get it. That's how you make money in SMB sales. But there's a cost to it, and I think we're hitting that cost now. **SARAH:** You mentioned volumes of 100,000+ fragmented prospects. That's a huge addressable market, but it's also incredibly scattered. How are you thinking about focusing your sales efforts? What's the actual beachhead right now? **KEVIN:** We're strongest in general dentistry. About 70 percent of our customers are GP practices with 5 to 15 dentists. We have some specialty practices—orthodontists, periodontists, pediatric dentists. But that's fragmented. Each specialty has its own needs, its own workflows, its own buyer ecosystem. Right now, we're trying to go deeper in general dentistry. We figure if we can dominate that segment, we can expand to specialty. But "dominating" is hard when you're up against private equity-backed competitors, against legacy systems that already have 80 percent adoption in a market, against the dental school that recommends a competitor to new graduates. We're also starting to think about geographic expansion. We've got good penetration in the Midwest and Southeast. West Coast is a gap. Northeast is competitive. So we're deploying reps to new metros, but again, it's the same problem. You need enough density to make territory economics work, but not so much density that reps are cannibalizing each other's deals. **SARAH:** How are you thinking about channel strategy to help with that coverage gap? **KEVIN:** That's where the partner conversation comes back. We have this company, PracticeMate, that's a DSO operations platform. They've got relationships with like 50 DSOs. If PracticeMate was selling our software as part of their suite, we could get coverage into markets we don't have reps in. But our product integrates with their product. There's some technical stuff to figure out. And then there's the economics question. If PracticeMate is selling on our behalf and taking 30 percent, we're bringing in ARR at a lower margin, but at much lower cost. A partner deal might generate $200K in ARR and cost us almost nothing to close. A rep deal might generate $120K in ARR and cost us $110K in salary and commission. The math works out. But salespeople don't want to hear that partners are in the picture. They hear "partner channel" and they think "our commission pool is getting cut." So there's this internal resistance to actually building out the partner channel strategy properly. **SARAH:** Internal sales resistance to partner programs is real. How are you getting past that? **KEVIN:** Honestly, we're not. That's a problem we need to solve, and I know it. The head of sales is incentivized on rep productivity. The CFO is incentivized on margin. I'm trying to think longer-term about what scales, but in the next 12 months, we're probably going to stick with rep-led sales and partner programs as a side play. It's not the optimal strategy, but it's less disruptive. **SARAH:** Let's go back to the demo-to-close conversion decline. You said it's dropped from 40 percent to 18-20 percent. That's a significant change, and that's directly affecting your revenue. What are you actually doing to turn that around? **KEVIN:** We've been doing a few things. We hired a demo engineer who's redesigning our demo flow. Instead of showing every feature, we're trying to do more diagnostic demos where we understand the prospect's problem first and then show relevant parts of the product. We're also working on demo scripts. We realized some reps are just hitting the "play" button on a screen recording. They're not actually selling during the demo. We want them to be asking questions, getting feedback, creating a conversation, not a presentation. And we're looking at the competitive landscape. We're getting beat by one competitor in particular who has this integration ecosystem that we don't have. They've got integrations with accounting software, patient communication platforms, all the stuff that practice owners care about. We're working on partnerships and integrations, but it takes time. **SARAH:** So it's product, process, and competitive. That's a lot to move the needle on simultaneously. **KEVIN:** Yeah, it is. And I'm not sure any one of those is going to be the silver bullet. I think the real issue is that the market is maturing. We're no longer the innovative vendor that practice owners haven't seen before. We're one of many. So we have to be better on all three fronts—product, sales, support—to win the deals we used to win easily. **SARAH:** Given all of this—the ACVs, the fragmented market, the competitive pressure, the conversion decline, the partner cannibalization—what's your ideal state in 18 months? **KEVIN:** [pause] Honestly, I'd like to be in a position where we're not growing headcount as fast. I'd like to have a partner channel that's generating 25 to 30 percent of new ARR. I'd like to see our demo-to-close conversion back to 30 percent. And I'd like to be clearer about our target customer. If I could somehow focus the sales org on just high-potential customers—practices that are really motivated to change, that fit our product perfectly, that have the budget—I think we'd be more efficient. But that means saying "no" to opportunities, and that's hard when you're trying to hit growth targets. We'd also benefit from a smarter lead generation approach. Instead of these broad-based Facebook ads and cold calling, what if we could get more referral-based or partner-sourced deals? Those tend to be higher quality and convert better. **SARAH:** That's a really practical vision. Let me ask the last thing—what would actually help you get there? From a sales and revenue perspective, what's missing? **KEVIN:** Three things, honestly. First, we need better market intelligence. We need to understand which segments of practices are most likely to buy, what the buying triggers are, what the buyers' criteria really are. We're making assumptions, but we're not testing them systematically. Second, we need to professionalize our go-to-market strategy. Right now, we're sort of doing everything—direct sales, partner programs, marketing—but none of it is really optimized. We need someone or a team who can think holistically about the revenue model and make tradeoffs. Third, we need tools that help our reps be more efficient and effective. We're using some CRM tools, but they're not giving us visibility into what's really happening in the deals. Why are we losing? What are buyers really evaluating? Where's the friction in our process? If we had those three things, I think we could probably cut our acquisition cost in half while improving conversion rates. That would completely change our unit economics. **SARAH:** Kevin, this has been incredibly helpful. I really appreciate you being so candid about the challenges. Before we wrap, is there anything else you think is important for us to understand about your business or your market? **KEVIN:** Just one more thing. Don't sleep on the people side of this. Sales is ultimately about trust and relationships. The tech and the tools help, but a great sales org is built on great people who understand their customers. In SMB, especially with owner-operators, that matters even more. We've been trying to scale sales like it's a machine where you hire more headcount and you get more output. But it doesn't work that way. You need to hire the right people, train them well, give them the autonomy to sell in a way that fits the customer, and then hold them accountable. It's harder than just hiring bodies, but the ROI is so much better. The other thing is, don't forget that your customers are people running businesses. They're not personas. They're not CLV curves. They're practice owners who are trying to grow their business, manage their team, pay their bills. If you lose sight of that human element, you'll lose the sale. **SARAH:** That's a perfect place to end. Thank you so much, Kevin. **KEVIN:** Thanks for asking good questions. This is a fun conversation. --- ## Key Takeaways Summary ### Revenue Model & Unit Economics - **ACV Challenge:** $8K–$12K ACVs require high-velocity sales model (40–50 deals per rep) - **Profitability Ceiling:** At $400K–$500K ARR per rep, adding more reps below that threshold breaks unit economics - **Growth Constraint:** Can't hire unlimited headcount; unsustainable at current ACV range without operational changes ### Market Fragmentation & Segmentation - **100,000+ Addressable Market:** Highly fragmented across DSOs, independents, and solo practitioners with vastly different economics - **Segment Mismatch:** Same sales approach doesn't work across $5K solo practices vs. $100K+ DSO deals - **Coverage Gap:** Geographic expansion creates density challenges; untapped markets require new infrastructure ### Sales Productivity & Rep Quality - **Volume vs. Quality Trade-off:** High-velocity model (3–4% lead-to-opportunity conversion) conflicts with relationship selling needed for owner-operators - **Outlier Performance:** Top performers (like Jessica) achieve 45% opportunity-to-close rates through consultative approach, but this doesn't scale - **Onboarding Complexity:** Dental practice owner psychology requires specialized training; junior reps struggle without mentorship ### Demo-to-Close Conversion Decline - **Dramatic Decline:** 40% (2 years ago) → 35–40% (1 year ago) → 18–20% (current) - **Root Causes:** Product commoditization, competitive parity, social proof issues, demo quality inconsistency - **Buyer Behavior Shift:** Prospects more cautious; willing to verify with existing customers; referrals with caveats reduce deal confidence ### Channel Partner Cannibalization - **Territorial Conflict:** Reps targeting accounts within partner networks; unclear account rules - **Lost Revenue:** DSO deal ($160K ARR) lost entirely due to internal misalignment and partner frustration - **Partner Economics Tension:** Partners want exclusivity; sales leadership wants flexibility; no clear governance model ### Owner-Operator Buying Psychology - **Personal Risk Perception:** Business is personal; switching costs are emotional and reputational, not just financial - **Trust > Features:** Buyers prioritize vendor reliability and relationship over feature checklist - **Implementation Anxiety:** Owner responsible for managing implementation risk; vendor lock-in feels permanent - **Non-Technical Decision Maker:** Owner is buyer, but often less tech-native than their office manager or operations team ### Strategic Gaps & Priorities - **Market Intelligence:** Lack of systematic data on buying triggers, buyer criteria, and high-potential segments - **Go-to-Market Strategy:** No unified revenue model; direct sales, partners, and marketing operating independently - **Sales Tooling:** CRM tools don't provide visibility into deal dynamics, loss reasons, or process friction ### 18-Month Vision - Reduce rep headcount growth trajectory while building partner channel (25–30% of new ARR) - Improve demo-to-close conversion back to 30%+ through better qualification and diagnostic selling - Sharpen target customer definition to improve sales efficiency and acquisition cost - Implement smarter lead generation (referral-based, partner-sourced vs. broad-based campaigns)