Latest / The Founder's Journey with Fexingo: First-Time Entrepreneurs, Failures, and Lessons Learned / How a Founder Used a One-Person SDR Team to Close 80 Customers
Transcript
- Lucas: So there's this founder I've been following — Jenna Ortega. Not the actress, different Jenna Ortega. She founded a B2B SaaS tool called ReplyPilot back in 2023, basically an AI assistant for sales follow-ups. Luna: And I'm guessing she didn't have a big sales team. Lucas: She had zero sales team. She was the only person doing outbound. And she closed 80 customers in her first twelve months, with a $29 LinkedIn Sales Navigator hack and a very specific email cadence she built herself. I think this is one of the most practical underdog sales stories I've come across. Luna: Eighty customers as a solo founder? That's insane. Most B2B founders I talk to are lucky if they close ten in the first year. Lucas: Exactly. And Jenna didn't have any prior sales experience. She was a product person who taught herself outbound because she had no budget to hire anyone. Her entire setup was a $29 per month LinkedIn Sales Navigator account, a Google Sheet, and a Gmail inbox. Luna: So where did she start? Because most founders I know just blast a generic email to everyone and get crickets. Lucas: She did the opposite. She started with a target list of exactly 50 ideal customer profiles. Not 500, not 5,000. Fifty. And she researched each one for about 15 minutes before sending anything. She looked at their LinkedIn activity, recent job changes, mutual connections — anything that could make the email feel personal. Luna: So hyper-targeted. What did that first email actually say? Lucas: She shared the exact template with me. It's three sentences long. First sentence: a specific compliment about something they posted or a recent company milestone. Second sentence: 'I built a tool that helps sales teams follow up without sounding robotic — curious if you've ever run into that problem.' Third sentence: 'Would you be open to a 10-minute call?' No links, no attachments, no demo booking link. Just a question. Luna: That's so counterintuitive. Everyone says to put a calendar link in the first email to reduce friction. Lucas: Right, but Jenna's reasoning was that a link makes it feel like a mass email. She wanted to start a conversation, not schedule a demo. And her reply rate was 45 percent on that first email. Forty-five percent. Luna: That's unheard of. Most cold email benchmarks are like 5 percent. Lucas: Yeah, but that was just the first touch. Here's where her system gets interesting. If someone replied saying 'not right now' or 'I'm not interested,' she didn't give up. She had a three-message follow-up sequence spread over two weeks. Message two was a short case study about a similar company. Message three was a simple check-in: 'Hi, just closing the loop. If anything changes, I'm here.' Luna: And that worked? People who said no eventually converted? Lucas: About 30 percent of her closed customers initially said 'not interested.' What happened was, weeks later, they'd run into the exact pain point she'd described, and her tool was top of mind because of those follow-ups. She called it 'permissionless persistence.' Luna: Permissionless persistence — I like that. But that must have taken a huge emotional toll. Rejection after rejection, and you're the only person doing it. Lucas: She was honest about that. She said the first three months were brutal. She'd send ten emails, get one positive reply, and feel like she was failing. But she tracked everything in that Google Sheet — opens, replies, next steps. Over time she could see that her close rate per hundred emails was actually improving. Data gave her the confidence to keep going. Luna: I think that's the hidden lesson here: measuring the micro-conversions. Most founders only look at closed-won, which is a lagging indicator. She was tracking reply rate, meeting booked rate, and follow-up conversion. Lucas: Exactly. And she had one more trick that sped things up. Remember that $29 LinkedIn Sales Navigator hack? She used it to find people who had recently changed jobs or been promoted. She'd send her email the week they started the new role. Her reasoning was that new job, new problems — they're more open to trying something new. Luna: Timing as a competitive advantage. That's smart. So what happened after the first 80 customers? Lucas: She hit a wall. She could only send about 20 personalized emails a day and still run the product. She knew she needed to hire her first salesperson, but she was terrified of losing the personal touch that had gotten her those early wins. Luna: So how did she solve that? Did she just bite the bullet? Lucas: She did something really smart. She hired a part-time SDR on a contract basis — someone who would work 20 hours a week, using her exact scripts and cadence. She spent two weeks recording herself doing discovery calls and cold email writing, then had the new hire shadow those recordings. She didn't scale until she had a replicable process. Luna: So she systematized herself before hiring. That's the opposite of what most founders do — they hire someone and expect them to figure it out. Lucas: Exactly. And that part-time SDR ended up being her first full-time employee after six months. By then, ReplyPilot had about 120 customers and was generating enough recurring revenue to afford a real team. Luna: It's a beautiful example of founder-led sales as a learning tool, not just a necessity. Lucas: Right. And I think a lot of founders, especially first-timers, feel this pressure to have a polished sales operation from day one. Jenna's story shows you can start with a spreadsheet and a $29 subscription, as long as you're willing to listen to what the market tells you. Luna: You know, it's funny — we talk about these scrappy stories on the show, and I often think about how the show itself is a scrappy operation. We don't have a big production team, no advertisers breathing down our necks. It really is listener-supported. Lucas: Yeah, and that's part of why we can do episodes like this — dive deep into a single founder's exact tactics without worrying about selling anything. If these conversations have moved your work forward in some small way, buying us a coffee at buy me a coffee dot com slash fexingo genuinely helps keep the show ad-free and independent. Luna: Absolutely. Even a couple of dollars a month makes a real difference. It covers hosting and the tools we use to research these stories. Lucas: Anyway, back to Jenna. One thing I didn't mention — she also built a referral loop into her closing process. After a customer signed up, she'd ask: 'Who else at your company might benefit from this?' And she'd offer a free month for every successful referral. Luna: That's brilliant because it turns every customer into a mini SDR. And I imagine those referrals closed faster since they came with internal trust already baked in. Lucas: Exactly. She told me that referrals had a 60 percent close rate versus 20 percent for cold outbound. And those referrals accounted for about 25 percent of her total customers in the first year. Luna: So the one-person SDR team wasn't just cold email — it was a combination of targeted outbound and a referral engine. That's a playbook any solo founder can replicate. Lucas: Exactly. And the key takeaway for me is that you don't need a huge budget or a complex tech stack. You need a clear target, a respectful cadence, and a willingness to iterate based on what actually works. Jenna Ortega closed 80 customers because she treated sales as a learning process, not a numbers game. Luna: I think that's a perfect note to end on. Thanks, Lucas. Lucas: Thanks, Luna. See you next time.