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Sep 5, 2023 · 18m · top-founders

How He Doubled Revenue To $2.4m Using a 5 Page Google Doc over the past 12 months

Adam Baker · 10m spoken Nathan Latka · 5m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Nathan Latka interviews Dealpad.io founder Adam Baker on how he scaled his buyer collaboration SaaS platform to a $2.4M ARR run rate with a lean 16-person team. Baker reveals his disciplined bootstrapping strategy, LinkedIn outbound prospecting engine, and the living 5-page Google Doc playbook driving remote sales execution.

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 34% of the talking time here. How this is scored →

Nathan as informed peer 5.2 Guest teaching 4.6 Guest disagreement 1.6 Nathan pushing back 2.4
05100:0010:001:14–3:47 · Nathan as informed peer 5/10 Defining the Buyer Collaboration Platform Category Nathan introduces Dealpad and asks Adam to clarify the category concept of buyer collaboration software. Adam cleanly breaks down internal tools like Gong versus external buyer collaboration, and Nathan tracks his revenue progression from previous appearances.3:49–6:21 · Nathan as informed peer 4/10 LinkedIn Outbound Engine and Lead Qualification Workflow Adam details his exact LinkedIn outbound tactic of following high-follower CROs and harvesting commenters. Nathan drills into manual versus automated steps and confirms tooling like Connected.io.6:22–8:24 · Nathan as informed peer 6/10 Team Composition, Quota Setting, and Sales Compensation Structure Nathan breaks down team headcount and quota-setting economics for newly hired AEs. He demonstrates solid SaaS expertise by immediately converting quota and base salaries into standard OTE and multiple targets.8:26–13:15 · Nathan as informed peer 5/10 Remote Sales Governance and the Living Google Doc Playbook Nathan queries how remote sales documents and scripts stay unified, prompting Adam to explain his weekly call-listening cadence and five-page Google doc framework. Adam educates Nathan on open versus closed questions and short discovery call tactics.13:16–17:01 · Nathan as informed peer 6/10 The Challenger Methodology and Venture Capital vs Debt Adam discusses the Challenger Sale methodology and critiques unicorn-chasing venture capital expectations versus realistic bootstrapped SaaS outcomes. Nathan enthusiastically affirms and validates Adam's take on building and selling mid-market SaaS companies.1:14–3:47 · Guest teaching 4/10 Defining the Buyer Collaboration Platform Category Nathan introduces Dealpad and asks Adam to clarify the category concept of buyer collaboration software. Adam cleanly breaks down internal tools like Gong versus external buyer collaboration, and Nathan tracks his revenue progression from previous appearances.3:49–6:21 · Guest teaching 5/10 LinkedIn Outbound Engine and Lead Qualification Workflow Adam details his exact LinkedIn outbound tactic of following high-follower CROs and harvesting commenters. Nathan drills into manual versus automated steps and confirms tooling like Connected.io.6:22–8:24 · Guest teaching 3/10 Team Composition, Quota Setting, and Sales Compensation Structure Nathan breaks down team headcount and quota-setting economics for newly hired AEs. He demonstrates solid SaaS expertise by immediately converting quota and base salaries into standard OTE and multiple targets.8:26–13:15 · Guest teaching 6/10 Remote Sales Governance and the Living Google Doc Playbook Nathan queries how remote sales documents and scripts stay unified, prompting Adam to explain his weekly call-listening cadence and five-page Google doc framework. Adam educates Nathan on open versus closed questions and short discovery call tactics.13:16–17:01 · Guest teaching 5/10 The Challenger Methodology and Venture Capital vs Debt Adam discusses the Challenger Sale methodology and critiques unicorn-chasing venture capital expectations versus realistic bootstrapped SaaS outcomes. Nathan enthusiastically affirms and validates Adam's take on building and selling mid-market SaaS companies.1:14–3:47 · Guest disagreement 1/10 Defining the Buyer Collaboration Platform Category Nathan introduces Dealpad and asks Adam to clarify the category concept of buyer collaboration software. Adam cleanly breaks down internal tools like Gong versus external buyer collaboration, and Nathan tracks his revenue progression from previous appearances.3:49–6:21 · Guest disagreement 1/10 LinkedIn Outbound Engine and Lead Qualification Workflow Adam details his exact LinkedIn outbound tactic of following high-follower CROs and harvesting commenters. Nathan drills into manual versus automated steps and confirms tooling like Connected.io.6:22–8:24 · Guest disagreement 1/10 Team Composition, Quota Setting, and Sales Compensation Structure Nathan breaks down team headcount and quota-setting economics for newly hired AEs. He demonstrates solid SaaS expertise by immediately converting quota and base salaries into standard OTE and multiple targets.8:26–13:15 · Guest disagreement 2/10 Remote Sales Governance and the Living Google Doc Playbook Nathan queries how remote sales documents and scripts stay unified, prompting Adam to explain his weekly call-listening cadence and five-page Google doc framework. Adam educates Nathan on open versus closed questions and short discovery call tactics.13:16–17:01 · Guest disagreement 3/10 The Challenger Methodology and Venture Capital vs Debt Adam discusses the Challenger Sale methodology and critiques unicorn-chasing venture capital expectations versus realistic bootstrapped SaaS outcomes. Nathan enthusiastically affirms and validates Adam's take on building and selling mid-market SaaS companies.1:14–3:47 · Nathan pushing back 2/10 Defining the Buyer Collaboration Platform Category Nathan introduces Dealpad and asks Adam to clarify the category concept of buyer collaboration software. Adam cleanly breaks down internal tools like Gong versus external buyer collaboration, and Nathan tracks his revenue progression from previous appearances.3:49–6:21 · Nathan pushing back 2/10 LinkedIn Outbound Engine and Lead Qualification Workflow Adam details his exact LinkedIn outbound tactic of following high-follower CROs and harvesting commenters. Nathan drills into manual versus automated steps and confirms tooling like Connected.io.6:22–8:24 · Nathan pushing back 3/10 Team Composition, Quota Setting, and Sales Compensation Structure Nathan breaks down team headcount and quota-setting economics for newly hired AEs. He demonstrates solid SaaS expertise by immediately converting quota and base salaries into standard OTE and multiple targets.8:26–13:15 · Nathan pushing back 3/10 Remote Sales Governance and the Living Google Doc Playbook Nathan queries how remote sales documents and scripts stay unified, prompting Adam to explain his weekly call-listening cadence and five-page Google doc framework. Adam educates Nathan on open versus closed questions and short discovery call tactics.13:16–17:01 · Nathan pushing back 2/10 The Challenger Methodology and Venture Capital vs Debt Adam discusses the Challenger Sale methodology and critiques unicorn-chasing venture capital expectations versus realistic bootstrapped SaaS outcomes. Nathan enthusiastically affirms and validates Adam's take on building and selling mid-market SaaS companies.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 66.1% · guest 33.9%0:00 · Nathan 66.1% · guest 33.9%3:00 · Nathan 25.1% · guest 74.9%3:00 · Nathan 25.1% · guest 74.9%6:00 · Nathan 31.2% · guest 68.8%6:00 · Nathan 31.2% · guest 68.8%9:00 · Nathan 22.9% · guest 77.1%9:00 · Nathan 22.9% · guest 77.1%12:00 · Nathan 14.8% · guest 85.2%12:00 · Nathan 14.8% · guest 85.2%15:00 · Nathan 29.7% · guest 70.3%15:00 · Nathan 29.7% · guest 70.3%18:00 · Nathan 96.8% · guest 3.2%18:00 · Nathan 96.8% · guest 3.2%
Sharpest disagreement ▶ 16:05 Dismissing VC unicorn culture

Adam forcefully pushes back on the conventional venture narrative, pointing out that 99.9% of companies never hit $10M ARR and arguing VC-inflated expectations harm founders.

 Hardest push from Nathan ▶ 5:02 Nathan pressing on manual outbound steps

Nathan challenges Adam's claim about manual LinkedIn research, questioning the feasibility of clicking through hundreds of likes manually until Adam admits to using Connected.io.

 Biggest teaching moment ▶ 11:31 Adam roleplaying open vs closed question discovery

Adam gives Nathan a rapid tutorial on cold-calling psychology, contrasting open and closed question phrasing with specific situational examples.

 Nathan holds their own ▶ 7:49 Nathan calculating OTE structure in real time

Nathan instantly computes and summarizes the sales compensation model from Adam's $100k base and $600k revenue target into exact OTE and quota multiples.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Defining the Buyer Collaboration Platform Category 5412 Nathan introduces Dealpad and asks Adam to clarify the category concept of buyer collaboration software. Adam cleanly breaks down internal tools like Gong versus external buyer collaboration, and Nathan tracks his revenue progression from previous appearances.
LinkedIn Outbound Engine and Lead Qualification Workflow 4512 Adam details his exact LinkedIn outbound tactic of following high-follower CROs and harvesting commenters. Nathan drills into manual versus automated steps and confirms tooling like Connected.io.
Team Composition, Quota Setting, and Sales Compensation Structure 6313 Nathan breaks down team headcount and quota-setting economics for newly hired AEs. He demonstrates solid SaaS expertise by immediately converting quota and base salaries into standard OTE and multiple targets.
Remote Sales Governance and the Living Google Doc Playbook 5623 Nathan queries how remote sales documents and scripts stay unified, prompting Adam to explain his weekly call-listening cadence and five-page Google doc framework. Adam educates Nathan on open versus closed questions and short discovery call tactics.
The Challenger Methodology and Venture Capital vs Debt 6532 Adam discusses the Challenger Sale methodology and critiques unicorn-chasing venture capital expectations versus realistic bootstrapped SaaS outcomes. Nathan enthusiastically affirms and validates Adam's take on building and selling mid-market SaaS companies.

Statements from this episode (12)

Assertion Not checkable as stated
Baker: Dealpad has grown to just over 160 customers
“We've got about a 160 now, just over a 160.”
Adam Baker Sep 5, 2023 ▶ 2:24
Assertion Not checkable as stated
Baker: Dealpad booked $400K ARR in 2021 and $1.2M in 2022
“Essentially in our first year, which was 21, we booked about 400 K of ARR. Last year we did about 1.2.”
Adam Baker Sep 5, 2023 ▶ 3:27
Prediction Not checkable as stated
Baker: Dealpad will finish 2023 between $2.7M and $3M in ARR
“And this year we're going to finish on about two point, anywhere between 2.7 and three.”
Adam Baker Sep 5, 2023 ▶ 3:38
Disclosure
Dealpad.io uses Connected.io to automate LinkedIn outbound outreach
“We use a software connected.”
Adam Baker Sep 5, 2023 ▶ 5:18
Disclosure
Dealpad.io has four SDRs spend one hour daily prospecting on LinkedIn
“Our SDRs carve out a piece of their day every single day to do this inside LinkedIn. Nathan Latka: How many SDRs? Adam Baker: we've got four. Nathan Latka: And how much time do you require they do this on LinkedIn? Adam Baker: An hour a day.”
Adam Baker Sep 5, 2023 ▶ 5:29
Assertion Not checkable as stated
Baker: Dealpad's Total Team Size Is 16 People
“We're 16.”
Adam Baker Sep 5, 2023 ▶ 6:27
Disclosure
Baker: Only Account Executives Carry Quotas at Dealpad
“Only the AAs carry quota.”
Adam Baker Sep 5, 2023 ▶ 6:56
Insight
Baker: Dealpad Targets $600K Quota for a $100K Base AE
“In terms of quota, it depends on how much you pay them, and so, so typically, you know, if I'm paying an AE a hundred K, I want 600 K in revenue back from that a year.”
Adam Baker Sep 5, 2023 ▶ 7:37
Insight
Baker: Dealpad reps never ask closed questions on sales calls
“We never ask closed questions, so we're always asking open questions to try and open them up.”
Adam Baker Sep 5, 2023 ▶ 11:26
Disclosure
Dealpad caps initial cold calls at 10 minutes maximum
“So we try and keep those, we call them, so this stage is a cold call, and we try and keep that down to 10 minutes max, and so either we try and qualify them on that first call if we need more time, we'll set that as a second step but typically we try and optim…”
Adam Baker Sep 5, 2023 ▶ 12:43
Insight
Building a $100M business requires multiple VC rounds, says Adam Baker
“If you really genuinely think that you could build a hundred million dollar business, then you're probably going to want to go out to venture money because you're going to need to raise two or three times. And debt probably won't help you do that over the long…”
Adam Baker Sep 5, 2023 ▶ 15:21
Opinion
Baker: VC obsession with unicorns harms founders building $10M–$20M ARR companies
“I think the expectations of these venture-led investors particularly are just completely skewed to these unicorns and these outliers. And it doesn't help founders who are building great companies who are, you know, 10 or on their way to ten million revenue cou…”
Adam Baker Sep 5, 2023 ▶ 16:23
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