Proposify

company on 1 show · 37 statements across 4 episodes · said 29 times in 8 episodes since 2017

Top Founders 29

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Top Founders 29

2024 4 mentions in 3 episodes 1 per episode
2021 13 mentions in 1 episode
2017 12 mentions in 4 episodes 3 per episode

every mention on every show, scene by scene, with the transcript →

37 statements about Proposify, every show

TOP FOUNDERS Disclosure
Proposify Lost Deals Lacking SSO Until a Developer Solved It Quickly
“We were losing deals because we didn't have single sign-on. And, you know, every, you'd go into JIRA, and you'd find this ticket a mile long with all these comments of, like, why it's so hard, and we can't do it, and there's too much technical debt. And he jus…”
Kyle Racki Oct 29, 2024 ▶ 14:46 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Reached $58,000 in Profit in 2023 After Burning Millions
“And then in twenty-twenty-three we, you know, we went from burning millions to actually being profitable. Mind you, not by very much. About 58 K in profit.”
Kyle Racki Oct 29, 2024 ▶ 13:19 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS 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 Racki Oct 29, 2024 ▶ 13:07 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS Assertion Supported
Proposify Laid Off 25% of Its Workforce in January 2022
“January 22 is when I had to cut a quarter of our staff and announce that”
Kyle Racki Oct 29, 2024 ▶ 10:22 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Was Nine Months From Insolvency in 2021 Before Pivoting
“Actually in twenty-twenty-one, I brought on a COO and CFO, Kathy who's, who's really amazing, and she kind of looked at what we were doing. We had this, you know, huge burn rate. She looked at the growth, and she's like, you're running off a cliff. Like, you'r…”
Kyle Racki Oct 29, 2024 ▶ 9:53 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS 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 Racki Oct 29, 2024 ▶ 9:06 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Increased Average ACV From $3K to Between $10K and $30K
“We went from, you know, being able to sell at most a 3000 dollar a year ACV contract, up to now where we have a couple in the six figure range, but average would be more 10, 20, 30 K deals.”
Kyle Racki Oct 29, 2024 ▶ 6:43 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
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 Racki Oct 29, 2024 ▶ 6:00 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS 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 Racki Oct 29, 2024 ▶ 3:59 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS Disclosure
Founders Took $1M Each in Secondaries During Proposify's $3M 2018 Round
“Around 2018, my co-founder and I first close our first round of actual, you know, major investment capital. We take we take a million each in secondaries, you know, put three million on the balance sheet.”
Kyle Racki Oct 29, 2024 ▶ 3:23 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Received Zero LOIs During 2022 M&A Process After Buyers Retracted
“The SaaS market kind of crashed in twenty-twenty-two. Investors and acquirers started getting nervous, and suddenly I had this, you know, what was this big list of potential acquirers all pull out, not get a single LOI from anyone.”
Kyle Racki Oct 29, 2024 ▶ 1:54 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Revenue Declined in 2022 For First Time Since Finding PMF
“Our rate of growth had been declining year after year, and when the SaaS market changed around twenty-twenty-two is when we actually started to decline for the first time really since we found product market fit”
Kyle Racki Oct 29, 2024 ▶ 1:26 Founder stuck at $8m revenue, burning $400k/month shares Profit and Loss, How he turned things around with Proposify CEO Kyle Racki
Proposal platforms like Proposify and Lupio are partners, not competitors
“No, no, those are more for us, those are more partner potential. So so we they would typically like when you're a proposal can consist of multiple parts and multiple documents and typically like there would be some intro about your companies and financials, ho…”
Erling Lind Sep 3, 2024 ▶ 10:08 He Raised $3m at a $25m valuation, is that overpriced or just right?
TOP FOUNDERS Disclosure
Racki: Proposify manages SEO across 12-person marketing team without dedicated staff
“We don't really have anyone dedicated to SEO, but our marketing team sort of factors SEO work into all the work that they're doing. It's about a 12, 12 person marketing team.”
Kyle Racki Jan 23, 2021 ▶ 18:15 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Disclosure
Racki: Proposify aims to double ARR before considering acquisition offers
“Like we want to get to the point where we're doubling ARR total, you know, in a year's time. So I think when that happens, let's say one or two years out, we'd probably be in a better position to look at acquisition offers today.”
Kyle Racki Jan 23, 2021 ▶ 17:35 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Disclosure
Racki: Proposify operates near breakeven and preserves cash reserves
“I'd say we're, depending on the month, we're around the breakeven mark. Some months we're cashflow positive. You know, other, other times we essentially have the same amount in the bank that we did when we raised the money.”
Kyle Racki Jan 23, 2021 ▶ 16:40 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Assertion Not checkable as stated
Latka: Proposify has a 1:1 ratio of equity raised to ARR
“And then talking about, again, growth and aggressiveness moving forward, I would argue you guys have been pretty darn capital efficient with about, you know, call it a one to one ratio of equity raised to ARR that you've been able to generate.”
Nathan Latka Jan 23, 2021 ▶ 16:12 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS 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 Racki Jan 23, 2021 ▶ 15:01 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Assertion Not checkable as stated
Racki: Proposify enterprise tier generates 20% of ARR with negative net churn
“That healthy segment Is it only makes up 20% of our total ARR, but it's actually two percent of our logos. So we're finding, yeah, it's I mean, the logo churn on it is under one percent a month. The net MRR churn is -2.3%. The LTV is 85 K.”
Kyle Racki Jan 23, 2021 ▶ 11:45 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Assertion Not checkable as stated
Racki: Proposify's high-touch segment grew 98% in 2020 versus 7.2% self-serve
“So if you look at the AR and MRR from that high-tech group, that grew to 98% in twenty-twenty, whereas the self-serve segment grew about 7.2%.”
Kyle Racki Jan 23, 2021 ▶ 10:49 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Disclosure
Racki: Proposify shifts sales comp to annual targets with accelerators
“What it looks like now moving into 20, 21 is like, As opposed to resetting the commissions and the quotas every month, it's more of looking at annual targets and then accelerators once they surpass the sort of baseline target for the year. So essentially every…”
Kyle Racki Jan 23, 2021 ▶ 7:53 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Disclosure
Racki: Proposify prematurely hired 10 to 20 sales reps before downsizing
“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 po…”
Kyle Racki Jan 23, 2021 ▶ 7:17 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Assertion Not checkable as stated
Racki: Proposify ended 2020 at $564k MRR with 20% growth
“So we ended the year at 564,000 in MRR USD. So we saw a 20% growth in, in 2020.”
Kyle Racki Jan 23, 2021 ▶ 6:42 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Disclosure
Racki: CBGF bought out early Proposify investors and added $3M
“CBGF came to the table with essentially a proposition that would enable them to be bought out a hundred percent, get, get out completely and put put about Geez, I almost forget now, three million on the balance sheet.”
Kyle Racki Jan 23, 2021 ▶ 4:01 Proposify Hits $7m Revenue Driving Expansion Into 200 Enterprise Accounts with $10k+ ACV's
TOP FOUNDERS Disclosure
Proposify Will Avoid Raising Venture Capital to Preserve Its Profitable Culture
“I think for us, we feel like VC money will change a bit of the culture. It has to. So, where we're profitable, and we're still growing, I think we want to just keep, keep doing it organically for now, and not try to jump on the VC train.”
Kyle Racki Jan 2, 2017 ▶ 17:13 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Prediction Not checkable as stated
Proposify Projects Reaching $1.5 Million in Revenue for 2016
“And this year it'll be like 1.5 million.”
Kyle Racki Jan 2, 2017 ▶ 16:56 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Generated Approximately $551,000 in 2015 Revenue
“Last year's revenue was about 551,000 dollars.”
Kyle Racki Jan 2, 2017 ▶ 16:51 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Maintains 2 Percent Net MRR Churn and 4.5 Percent Customer Churn
“Churn right now, I mean, net MRR churn is just about two percent. Customer churn is under five, so it's about 4.5%.”
Kyle Racki Jan 2, 2017 ▶ 14:37 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Averages $1,000 LTV But Reaches $15,000 For High-Tier Accounts
“The lifetime value on average is about a thousand dollars and obviously that changes, you know, based on what tier you're on. So that's why we have salespeople following up with like the hundred dollar, 250 dollar a month plans because the lifetime value there…”
Kyle Racki Jan 2, 2017 ▶ 14:16 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Spends $10,000 Monthly on Paid Marketing While Prioritizing Organic Growth
“We only really spend, I mean, I say only, maybe that's a lot for some people, but we spend about 10,000 a month on, on paid marketing and put a lot more work into the organic stuff.”
Kyle Racki Jan 2, 2017 ▶ 13:24 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Converts 200 to 300 Customers Monthly From Daily Trials
“When we look at how many people are signing up for trials, we're getting about between a hundred and a 150 new signups a day. We tend to close about two or 300 of those.”
Kyle Racki Jan 2, 2017 ▶ 11:29 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
Targeting Competitor Comparison Searches Drove Proposify's Early Customer Acquisition
“That's actually a bit of an SEO hack too. That really helped us in the early days because people would search like BidSketch alternative or, you know you know, basically just people are searching for comparisons and we were the only ones who were writing pages…”
Kyle Racki Jan 2, 2017 ▶ 10:47 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
Proposify Differentiates From PandaDoc by Specifically Targeting Digital Agencies
“Panda doc is a kind of a general purpose document management system. They do signatures and you can, you know, have contracts and that kind of thing. But for us, we were kind of like laser focused on mainly the digital agency space and giving them the design t…”
Kyle Racki Jan 2, 2017 ▶ 10:11 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Stayed Under $1K MRR for 17 Months Before Product-Market Fit
“We were under one K MRR for quite a long time. How long? From about April 2013, we didn't really hit it until about September of 20 14, was when we started to see, you know, everything increase.”
Kyle Racki Jan 2, 2017 ▶ 3:25 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Nears $150,000 in Monthly Recurring Revenue
“Oh yeah. We're close to one a 150 K MRR.”
Kyle Racki Jan 2, 2017 ▶ 3:12 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Approaching 3,200 Paying Customers
“We're getting close to about 3200.”
Kyle Racki Jan 2, 2017 ▶ 2:53 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki
TOP FOUNDERS Assertion Not checkable as stated
Proposify Customers Pay $40 to $50 Monthly on Average
“The average customer pays about 40, 50 dollars a month, but we have prices ranging from 25 dollars a month all the way up to about 250 dollars a month.”
Kyle Racki Jan 2, 2017 ▶ 2:39 EP 527: Proposify Hits 3200 Customers and $150k in MRR with CEO Kyle Racki

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