Kyle Racki, CEO of proposal software platform Proposify, reflects on past go-to-market hiring mistakes in an interview with Nathan Latka.
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“We had raised the first time we had raised the round. We kind of did the classic mistake where you know, you go and hire a VP of sales with big company experience. They go and hire, you know, 10, 20 reps very quickly. Without much of our go to market or our positioning and figure it out. So I think we'd already made that mistake and taken the team back to a very small size.”
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More from Kyle Racki
Insight
Funded Founders Should Take Reasonable Salaries to Avoid Product-Harming Stress
“Because I think, especially when you raise money, you need to be reasonably comfortable. You know, you can't work on a product and hustle if you're worrying about how to pay your mortgage.”
Kyle RackiJan 2, 2017▶ 5:08EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
Disclosure
Proposify Bloated to 100 Employees on Just $5M to $6M Revenue
“We hired enough people that we were eventually around, you know, a hundred people or so, and for, you know, at the time, I think only a five or six million dollar business.”
Kyle RackiOct 29, 2024▶ 3:59Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
Insight
Mid-Market Proposal Software Buyers Prioritize Control and Management Over Aesthetics
“The customers who bought Proposify to send beautiful proposals and get faster sign-off, that messaging didn't really resonate with the mid-market, because they're like, we have cool PowerPoint decks, like, we know how to send proposals. What they really wanted…”
Kyle RackiOct 29, 2024▶ 6:00Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
Disclosure
Proposify Burned $400,000 Per Month While Generating Under $10M in ARR
“At one point, we were actually burning 400 K a month, which, you know, depends on your size, right? That might not seem a lot if you're a hundred million ARR, but if you're under ten million, that's a lot of money to be burning.”
Kyle RackiOct 29, 2024▶ 9:06Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
Disclosure
Kyle Racki Left Departed VP Roles Unfilled, Resuming Product and Marketing
“My VP of product quit, my VP of marketing quit. I didn't replace them. I just got in and started running product and marketing again just like in the early days.”
Kyle RackiOct 29, 2024▶ 13:07Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
Disclosure
Racki: Proposify focuses all product and engineering teams on enterprise accounts
“So essentially the whole company is aligned around this higher touch segment. We don't, you know, we don't break out engineering teams or product teams to say, well, you guys go after the low segment and you go after the high one. Everybody is building for the…”
Kyle RackiJan 23, 2021▶ 15:01Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
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