Join Pete in conversation with Karun Kaushik, Delve's Co-Founder and CEO.
Pete and Karun talk about "Selling to your uncle", first-principles sales motion evolution, systematizing growth hacks and more.
Delve's amazing growth from two MIT dropouts to hundreds of customers, millions in ARR, and a $32m Series A has lessons for everyone on their founder-led sales journey.
More on Delve here: https://delve.co/
Executive Summary
When Karun Kaushik and Selin Kocolar encountered compliance obstacles as MIT computer science students, they decided to build a better solution. Their company, Delve, helps startups complete SOC 2 compliance in ten hours instead of hundreds. With no sales background, these two founders generated over $1 million in ARR from their apartment before hiring their first salesperson. Their approach centered on treating every customer conversation like helping a family member make a good decision. This methodology helped them close a $32 million Series A with Insight Partners, demonstrating that systematic, customer-focused selling can outperform high-pressure tactics.
Key Metrics
Current Scale: $1M+ ARR achieved with two founder-sellers before first sales hire
Average Contract Value: $15,000, gradually increased as product value expanded
Sales Cycle: 2-3 calls over 2-3 weeks
Target Market: Pre-seed to Series C startups, slowly moving upmarket for stability
Deal Velocity: 20+ demos per account executive daily at current scale
Funding: $32 million Series A at $300 million valuation
Current Sales Team: Multiple account executives with 6-10 years experience each
Problem Discovery and Validation: Finding Real Pain Points Through Direct Customer Feedback
Kaushik and Selin started as roommates at MIT, both fascinated by AI and medicine. Their first project was an AI medical scribe, but they kept running into HIPAA compliance roadblocks. Instead of seeing this as just another startup obstacle, they spotted a real business opportunity.
Their approach was refreshingly straightforward: they believed compliance shouldn't take 80+ hours when a smart TurboTax-style interface could walk people through it much faster. The key insight? "We sold that dream before we had a product, built it around the customer, and then realized this could work," Karun explains.
Their first customer was a small Y Combinator healthcare company, and here's how they closed them: pure hustle and honesty. No fancy product demos or slick presentations—just two founders willing to do whatever it took to solve the customer's problem. This fake-it-till-you-make-it approach worked because they delivered on their promises through intense personal involvement.
The move from HIPAA to SOC 2 wasn't really a pivot—it was smart market expansion. SOC 2 had way more potential customers while keeping the same core promise: making compliance way less painful.
Early Sales Process Development: Sell to Your Uncle (Seriously)
Kaushik's breakthrough in sales came through reframing customer interactions around a simple mental model: imagining every customer as his uncle. This shifted his mindset from "I need to convince this person to buy" to "I need to help this person make a good decision."
Think about it: you'd never sell your uncle something he doesn't actually need, right? And if you knew he was about to make a bad purchase decision, you'd definitely speak up. "If your product is the best, then you wouldn't let your uncle buy another product because he's just going to have a worse experience," Karun puts it.
This approach made their sales calls more natural and consultative. Instead of pitching features, Kaushik spent 80-90% of each conversation listening and asking questions. He would help prospects understand their compliance situation first, then—only if Delve was genuinely the right fit—explain why they should work together.
The framework included being honest when Delve wasn't the right solution. Sometimes Karun would recommend competitors or suggest prospects wait. This honesty built trust and often led to referrals or future business when timing improved.
The actual sales process evolved organically through constant tweaking. It started super basic—just Karun asking "Want to buy this?" with no follow-up. Then he kept asking "why didn't this deal close?" and fixed one thing at a time: added follow-up calls, started sending contracts, created email sequences. Each improvement made the whole system work a little better.
Skills Development: Learning Sales Like Learning Code
Neither Karun nor Selin had ever sold anything before, so they approached it like any other skill they needed to master: break it down, practice deliberately, and debug systematically.
"It took me a few months," Karun admits. "Sales is not a natural thing—you're being very direct and persuading people." But once he started thinking of customers as family members who deserved his honest advice, everything clicked.
Their learning toolkit was pretty straightforward: find a mentor who's done sales before, practice your pitch with them constantly, and watch recordings of your calls to spot what you're missing. Pete Kazanjy's "Founding Sales" became their bible—so much so that they eventually had their whole sales team read it to better understand how founders think.
The key insight? Most sales problems aren't huge dramatic issues. They're tiny paper cuts that add up. Maybe you're forgetting to book follow-up calls. Maybe your emails sound too formal. Maybe your contracts are confusing. Fix one small thing at a time, and suddenly your win rate jumps.
Sales Evolution Phases: From Hand-Drawn Fish to Million-Dollar ARR
Watching Delve's sales process evolve is like watching a startup grow up. They went through four distinct phases, each one solving the problems the previous phase created.
Phase One: The Apartment Days (0-20 customers) Picture this: Karun and Selin tracking deals with hand-drawn fish on Post-it notes stuck to their apartment wall. Each fish represented a closed deal with the dollar amount written on it. They called their apartment "the aquarium" and themselves "fishermen of compliance." Quirky? Absolutely. Effective? You bet—they could literally count their ARR by counting Post-it notes.
Phase Two: Getting Organized (20-50 customers) The Post-it system couldn't scale forever, so they moved to spreadsheets and started building real processes. Follow-up calls became standard. Contracts got sent systematically. Email sequences were born. Nothing fancy, but much more reliable than their apartment aquarium.
Phase Three: Real Tools for Real Growth (50-100 customers) HubSpot entered the picture for proper pipeline management. They started using Slack channels with customers (way faster than email). Gong helped them analyze what was actually happening on calls. This is when things started feeling like a real sales operation.
Phase Four: Automation Takes Over (100+ customers) The current setup includes Ergo for automated CRM updates (Karun calls it "the best product we've used this year"), Circle Back AI for meeting notes, and other tools that handle the boring stuff automatically. Now founders can focus on strategy instead of data entry.
Each transition happened naturally when the current system started breaking. No grand plans—just solve today's problems and keep moving forward.
Channel Strategy: Ping-Pong Shirts, Flying Planes Near Conferences, and Other Budget Growth Hacks
With limited budget and big ambitions, Delve had to get creative about finding customers. Their secret weapon? Understanding exactly where startup founders hang out online and then showing up with personality.
The Ping-Pong Power Move
Selin went to a ping-pong tournament wearing a custom t-shirt that said "Beat me in ping-pong and get $1,000 off compliance." She posted a photo on Twitter, which generated 50,000 views and $50,000 in revenue from four deals that closed the next day.
Cost of the campaign was minimal—essentially the price of the t-shirt. The return demonstrated how well-targeted, creative marketing could resonate with their founder audience.
More Creative Hits
The doormat campaign was particularly effective. Instead of the standard press release, they sent customers doormats that said "Your shoes look good, do your SOCs 2?" It generated three times the engagement of their later actual funding announcement.
The airplane banner campaign at SaaStr conference showed creative execution within constraints. The plane flew near SaaStr from Livermore, California (about an hour away from the actual conference) for thirty minutes. The banner said "SOC 2 Made Plane and Simple." While conference attendees didn't see the plane, the Twitter and LinkedIn photos generated significant online engagement for $3,000 versus $200,000 traditional sponsorship costs.
The Strategy Behind the Stunts
These campaigns worked because Delve understood their audience: startup founders who appreciate clever, resourceful marketing around typically dry topics like compliance. "Our customers are on Twitter and LinkedIn, so we just want to be super loud on Twitter and LinkedIn," Karun explains.
When organic channels started hitting their limits, they expanded thoughtfully. Word-of-mouth referrals, industry events, strategic partnerships—basically mapping out every way revenue could come in and prioritizing the easiest ones first.
Timing and Triggers: Identifying Customer Urgency
Delve's advantage came from recognizing the exact moment when startups need compliance help: when they land their first enterprise customer who requires SOC 2 certification.
These founders aren't casually shopping for compliance solutions—they need immediate help or risk losing a major deal.
Karun identified these moments through social media monitoring (founder posts about closing big deals), referral networks (other customers giving heads-ups), and proactive outreach to companies raising Series A rounds (which often triggers enterprise sales efforts).
The psychological positioning was just as important as the timing. Instead of feeling like a vendor trying to sell something, Karun positioned himself as "telling your friend to do something that you know is in their best interest." When someone needs help and you can actually solve their problem, the conversation changes completely.
Even small timing details mattered. Instead of asking "When can we meet?" he'd say "When are you free on Monday?" Much more specific, much less back-and-forth, much faster to get meetings scheduled.
Pricing and Positioning Evolution: Learning What People Will Actually Pay
Delve's pricing journey was pretty straightforward: start somewhere reasonable, then gradually increase prices as the product got better and customers saw more value. They began around $15,000 per customer and kept testing higher prices based on Y Combinator's advice about systematic price testing.
The positioning evolved too. Early on, they sold themselves as "compliance consulting with some AI help." As their automation improved, they shifted to "AI-powered compliance platform with expert oversight." The key was being honest about what was automated versus what still required human work—transparency built way more trust than overpromising.
Pricing conversations followed the uncle framework. Instead of defending their prices, Karun would put everything in context: "Think about the enterprise deal you might lose if compliance takes too long" or "Consider how much founder time is worth versus paying us to handle this." When you frame it as helping someone make a smart business decision rather than justifying a cost, the conversation goes much smoother.
As the product got better and their track record grew, they could charge more because customers genuinely got more value. Simple as that.
Customer Success Approach: The 5-Minute Response Rule
Delve's customer success approach centers on response speed, maintaining under 5-minute response times across all communication channels.
Karun compares this to roadside assistance: the company that responds in 2 minutes versus 2 hours creates a very different customer experience. Even when problems can't be solved immediately, quick acknowledgment makes customers feel heard and prioritized.
The psychological impact is significant. Even when problems can't be solved immediately, acknowledging customer messages quickly makes them feel heard and prioritized. "You must respond instantly and help customers actually solve their problems," Karun emphasizes.
Early on, Delve was essentially a customer success company that happened to have a product. Karun and Selin would do whatever it took to solve customer problems—hop on calls, fix things manually, whatever worked. Speed and flexibility were their competitive advantages over bigger, slower competitors.
As they scaled, they had to get more systematic about being proactive instead of just reactive. "CS is very proactive. It's not just responding to problems but checking in," Karun learned. The challenge became maintaining that personal touch while building scalable systems.
The biggest mistake? Assuming customer success would just happen automatically as they grew. It doesn't. You have to keep investing in it deliberately, or customers start feeling neglected.
Technology and Hiring: From Spreadsheets to $1M ARR Before Your First Sales Hire
Delve's tech stack evolved from "whatever works" to "whatever works automatically." They started with spreadsheets, moved to HubSpot for pipeline management, then added tools that eliminated the boring administrative stuff founders hate doing.
The current setup includes Ergo for automated CRM updates (which Karun absolutely loves), Circle Back AI for meeting notes, and Gong for call analysis. The key was choosing tools that made founder life easier, not more complicated.
When and How to Hire Your First Salesperson
Here's the big question every founder asks: when do you hire your first sales rep? For Delve, the answer was after Karun and Selin hit $1 million in ARR doing everything themselves from their apartment.
Why wait so long? Because you need to figure out what actually works before you hand it off to someone else. "You can't hire somebody else to figure out your sales motion for you," as the saying goes.
Their first hire had 8 years of experience and had actually worked at a competitor. This wasn't an accident—when you're selling to other founders, you need someone who can hold their own in those conversations. Founders can be tough customers, and they respect experience.
The hiring criteria were simple but important: hunger (how badly do they want this?), emotional intelligence (can they read the room?), and learning speed (how fast do they pick up new concepts?). They did week-long work trials to see how candidates actually performed, not just how they interviewed.
Getting New Salespeople Up to Speed
The onboarding process centered on knowledge transfer through recorded calls, feedback sessions, and gradual responsibility increases. They made sure everyone got equal pipeline allocation—no playing favorites, which just creates team drama.
The biggest mistake? Not giving their second and third hires the same detailed onboarding they gave their first rep. Consistency matters, and good people deserve good training regardless of when they join.
Results and Strategic Lessons: How Uncle-Based Selling Beat Traditional Sales Tactics
Delve's path from MIT dorm room to $32 million Series A demonstrates that systematic, customer-focused selling can be more effective than high-pressure tactics. Here's what other founders can learn from their approach.
The Core Insights That Drive Everything
First, treat sales like debugging code. When something isn't working, dig into why. Don't just try random fixes—identify the specific problem and solve it systematically. Karun's approach of asking "why did this deal not close?" after every loss led to incremental improvements that compounded over time.
Second, the uncle framework really works. When you genuinely care about helping customers make good decisions (even if that means recommending competitors sometimes), trust builds quickly. This consultative approach leads to higher win rates, better referrals, and customers who actually stick around.
Third, operational excellence in boring stuff creates real competitive advantages. Responding to messages in under 5 minutes, making contracts easy to understand, booking follow-up calls during live conversations—these details matter more than most founders think.
Fourth, creative marketing with limited budgets can work wonders if you understand your audience. Delve's viral campaigns succeeded because they knew exactly how startup founders think and what makes them laugh (or at least smile).
Practical Steps You Can Take Right Now
Want to implement some of this immediately? Here are the specific tactics that moved the needle for Delve:
Start scheduling 15-minute meetings instead of 30-minute ones (they'll usually run longer anyway, but the lower commitment gets more people to say yes). Book follow-up calls while you're still on the current call. Set up Slack channels with prospects instead of relying on email. Make your contracts look like marketing materials instead of legal documents. Text customers instead of just emailing them.
For customer success, speed trumps perfection. Acknowledge every message within 5 minutes, even if you can't solve the problem that fast. Set up systems that let you respond instantly—your customers will notice the difference.
The Bigger Picture Strategy
Delve's gradual move upmarket (from pre-seed to Series C customers) shows how to evolve your ICP thoughtfully. They're chasing bigger deals and more stable customers, but they're doing it systematically based on what they've learned, not just because bigger deals sound nice.
Their approach to automation follows the same pattern—automate the stuff that doesn't require human judgment, but keep founders involved in strategic decisions. This lets them scale without losing the personal touch that made them successful in the first place.
Bottom Line
Delve's success comes down to this: they built genuine relationships with customers, systematically improved everything that wasn't working, and never tried to skip steps in the process. Their $32 million Series A validates that authentic, systematic selling creates sustainable competitive advantages that are hard for competitors to copy.
For founders who are 18-24 months behind where Delve is now, the message is clear: focus on systematic process development and authentic customer relationships before you worry about hiring salespeople or buying fancy tools. Master the fundamentals first, then scale what works. That's how you build a sales machine that can grow with your company for years to come.
