Feb 5, 2016 · 21m · top-founders
Yesware Aims for $30m in 2016 with Matthew Bellows of Yesware
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Top, Nathan Latka interviews Yesware founder and CEO Matthew Bellows to dissect how the sales acceleration platform crossed a $10 million run rate and set sights on reaching $30 million in 2016. Bellows outlines Yesware's bottom-up product-led growth, sales quota benchmarks, venture funding strategy, and practical lessons for scaling enterprise SaaS.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 50.6% of the talking time here. How this is scored →
Nathan as informed peer 4.6 Guest teaching 4.6 Guest disagreement 1.4 Nathan pushing back 2.8
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 6:26 Correcting the run rate premise
Bellows directly corrects Latka's mistaken assertion that Yesware was merely aiming for $10M ARR in 2016, pointing out they were already well above $10M.
Hardest push from Nathan ▶ 13:28 Pressing on product adoption triggersLatka interrupts Bellows' generalized explanation to demand exact specifics on what 'catching on' inside an organization means in quantitative terms.
Biggest teaching moment ▶ 15:23 Real-world data versus SaaS blog theoryBellows provides an insightful reality check to founders, explaining that neat cohort analysis models and single 'magic bullet' activation metrics rarely exist in messy operational data.
Nathan holds their own ▶ 11:35 Calculating rep quota funnel capacityLatka swiftly computes the aggregate inbound requirement of 2,500 qualified leads per month based on rep headcount and uses it to pressure Bellows on paid acquisition channels.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Yesware Founding, Venture Capital, and Team Structure | 4 | 5 | 1 | 2 | Nathan references Bellows' background and articles, prompting advice for SaaS founders on sales processes. Bellows delivers structured guidance on why founders must personally close their first million before hiring sales reps. | |
| Yesware Run Rate and Target Market Definition | 4 | 4 | 2 | 3 | Nathan seeks exact revenue and user metrics, misinterpreting Bellows' run rate target which Bellows politely corrects. Bellows details their target market size and Census data analysis. | |
| Average Deal Sizes and Sales Allocation Models | 6 | 4 | 1 | 3 | Nathan drills into rep quotas and lead conversion mathematics, immediately computing the 2,500 qualified leads per month required across 25 reps. Bellows explains quota economics and their reliance on inbound organic channels. | |
| Product-Led Growth and Enterprise Land-and-Expand Strategy | 5 | 6 | 2 | 4 | Nathan presses on specific user activation triggers that signal enterprise readiness. Bellows demystifies SaaS literature, cautioning that real-world cohort and feature data are far messier than blog posts claim. | |
| Competitive Differentiation: Sales Acceleration vs Marketing Automation | 4 | 4 | 1 | 2 | Nathan asks about category positioning relative to CRMs and marketing automation platforms. Bellows distinguishes one-to-many marketing tools from one-to-one sales acceleration before wrapping up with the Famous Five. |
Statements from this episode (18)
Bellows: Yesware has 80 total employees and about 30 in product
“Total employees is 80. We have about 30 people in the product group, which are engineers, designers, and product owners.”
Bellows: Yesware employs roughly 25 to 30 sales staff
“We have about 25 or 30 folks in the sales department.”
Bellows: Founders should generate $1M in sales before hiring first rep
“My recommendation is that the founding team, whether that's If the engineer is the sort of CEO person, the partner, sell about a million dollars worth of product before you go out and sell and hire your first or second salesperson. You want to get to about a m…”
Bellows: Yesware counts approximately 750,000 registered users
“We have about, like you said, 750,000 registered users.”
Bellows: HBS case study documented Yesware at $7M ARR a year prior
“Harvard Business School did a case on Yesware, where we talked about, this would be about a seven million dollar company. That was about a year ago.”
Bellows: Google Apps represents roughly 5% of Yesware's total market
“Companies in the Google Apps world, which is about five percent of our total market.”
Bellows: Yesware targets companies with 1,000 to 2,000 employees
“Our target market is customer, you know, companies with a thousand to 2000 employees. Two to 300 sales people, and those are companies that we go after aggressively. We can do a little bit smaller companies, we can do a little bit larger, but that's kind of ou…”
Bellows: Yesware's average deal size is around $500 per month
“Our average deal size is around 500 dollars a month.”
Bellows: Yesware sales reps need 100 monthly leads to close 8-10 deals
“We look to give us each individual sales rep about a hundred leads a month. To close eight to 10 leads they need to make their quota.”
Bellows: Yesware reps carry a monthly quota of $4,000 in new MRR
“Yeah, our quota is, is 4000 dollars of new monthly recurring revenue a month.”
Bellows: 90% of Yesware's leads come from organic inbound channels
“We do a little bit of paid but I would say 90% of our leads are from inbound to the website, or inbound to the Chrome store, or the Google Apps marketplace. Those are our main channels.”
Bellows: Yesware uses organic individual adoption to qualify enterprise outbound leads
“Yeah, so, so, so if a company has 10 or 20 or 30 reps already using Yesware, and on, on average, you know, five to 10 will be paying reps, paying users who they will put in their credit card, that, that's a great lead for us. So, we want to spread this product…”
Bellows: SaaS usage data is messy, requiring intuition over clean metrics
“My, the real advice I would give to your listeners is don't be frustrated if things aren't crystal clear. Like, when I read the blog posts about doing cohort analysis, this is where I read the blog posts about finding the feature that determines whether or not…”
Bellows: Yesware partners with Salesforce, competes with InsideSales and ClearSlide
“We are a partner for Salesforce.com and other CRMs.
we compete with companies like Insidesales.com or ClearSlide or others that, you know, are also trying to make salespeople more effective with their software.”
Bellows: Marketing automation is one-to-many; sales acceleration is one-to-one
“Those people are sort of higher in the funnel, if you will.
Those are marketing automation companies, and so they focus on one-to-many marketing blasts and communications from a marketing group, and whereas we focus on the one-to-one between the salesperson a…”
Bellows aims for Yesware to hit a $30M ARR by end of 2016
“I would like to end the year at about a thirty million dollar run rate.”
Bellows: Yesware uses Reid Hoffman's 'The Alliance' framework for executive roles
“And we've just rolled that out to our executive team here as a framework. And it's really, it's a fantastic, helpful way to talk about how long people want to be at the company and what they're going to do in the next, in their next, what they call tour of dut…”