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May 8, 2021 · 21m · top-founders

Gainsight Paid Him $10k+ To Figure Out Sales in 2013, What He Recommends Now

Richard Harris · 12m spoken Nathan Latka · 6m spoken
0:00 / 0:00

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

SaaS sales advisor Richard Harris joins Nathan Latka to detail proven B2B sales methodologies, from founder-led sales and quota design to scaling expansion revenue, while sharing how he runs a profitable lifestyle consultancy.

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 32.6% of the talking time here. How this is scored →

Nathan as informed peer 4.8 Guest teaching 3.6 Guest disagreement 1.8 Nathan pushing back 3.0
05100:0010:0020:002:35–6:26 · Nathan as informed peer 4/10 Early Gainsight Engagement and Evolving Training Models Nathan inquires about Richard's early pricing and training model changes. Richard explains his transition to remote cohort-based reinforcement training, maintaining a friendly, cooperative dynamic.6:26–10:54 · Nathan as informed peer 7/10 Client Capacity, Lifestyle Balance, and Book Project Nathan introduces detailed data points from his previous interview with Gainsight's CEO, asking Richard to dissect where the sales system scales or breaks. Richard outlines why early sales processes must be treated as hypotheses and tested against customer feedback.10:54–13:55 · Nathan as informed peer 4/10 Founder-Led Sales and Strategic Early Hiring Nathan queries standard startup sales milestones, prompting Richard to emphatically advocate for founder-led sales up to early PMF and advise against prematurely hiring corporate VPs of sales.13:56–19:21 · Nathan as informed peer 7/10 Determining ACV Thresholds for Sales Interaction Nathan challenges Richard on the financial viability of touch sales at low ACVs and pushes past non-committal answers regarding expansion quota models. Richard adapts by giving concrete thresholds and splitting quota structures between AMs and CSMs.19:21–20:35 · Nathan as informed peer 2/10 The Famous Five Rapid-Fire Questions Nathan runs through the standard closing rapid-fire format. Richard shares personal background, book habits, and advice on listening to others.2:35–6:26 · Guest teaching 3/10 Early Gainsight Engagement and Evolving Training Models Nathan inquires about Richard's early pricing and training model changes. Richard explains his transition to remote cohort-based reinforcement training, maintaining a friendly, cooperative dynamic.6:26–10:54 · Guest teaching 4/10 Client Capacity, Lifestyle Balance, and Book Project Nathan introduces detailed data points from his previous interview with Gainsight's CEO, asking Richard to dissect where the sales system scales or breaks. Richard outlines why early sales processes must be treated as hypotheses and tested against customer feedback.10:54–13:55 · Guest teaching 5/10 Founder-Led Sales and Strategic Early Hiring Nathan queries standard startup sales milestones, prompting Richard to emphatically advocate for founder-led sales up to early PMF and advise against prematurely hiring corporate VPs of sales.13:56–19:21 · Guest teaching 4/10 Determining ACV Thresholds for Sales Interaction Nathan challenges Richard on the financial viability of touch sales at low ACVs and pushes past non-committal answers regarding expansion quota models. Richard adapts by giving concrete thresholds and splitting quota structures between AMs and CSMs.19:21–20:35 · Guest teaching 2/10 The Famous Five Rapid-Fire Questions Nathan runs through the standard closing rapid-fire format. Richard shares personal background, book habits, and advice on listening to others.2:35–6:26 · Guest disagreement 1/10 Early Gainsight Engagement and Evolving Training Models Nathan inquires about Richard's early pricing and training model changes. Richard explains his transition to remote cohort-based reinforcement training, maintaining a friendly, cooperative dynamic.6:26–10:54 · Guest disagreement 2/10 Client Capacity, Lifestyle Balance, and Book Project Nathan introduces detailed data points from his previous interview with Gainsight's CEO, asking Richard to dissect where the sales system scales or breaks. Richard outlines why early sales processes must be treated as hypotheses and tested against customer feedback.10:54–13:55 · Guest disagreement 2/10 Founder-Led Sales and Strategic Early Hiring Nathan queries standard startup sales milestones, prompting Richard to emphatically advocate for founder-led sales up to early PMF and advise against prematurely hiring corporate VPs of sales.13:56–19:21 · Guest disagreement 3/10 Determining ACV Thresholds for Sales Interaction Nathan challenges Richard on the financial viability of touch sales at low ACVs and pushes past non-committal answers regarding expansion quota models. Richard adapts by giving concrete thresholds and splitting quota structures between AMs and CSMs.19:21–20:35 · Guest disagreement 1/10 The Famous Five Rapid-Fire Questions Nathan runs through the standard closing rapid-fire format. Richard shares personal background, book habits, and advice on listening to others.2:35–6:26 · Nathan pushing back 2/10 Early Gainsight Engagement and Evolving Training Models Nathan inquires about Richard's early pricing and training model changes. Richard explains his transition to remote cohort-based reinforcement training, maintaining a friendly, cooperative dynamic.6:26–10:54 · Nathan pushing back 4/10 Client Capacity, Lifestyle Balance, and Book Project Nathan introduces detailed data points from his previous interview with Gainsight's CEO, asking Richard to dissect where the sales system scales or breaks. Richard outlines why early sales processes must be treated as hypotheses and tested against customer feedback.10:54–13:55 · Nathan pushing back 2/10 Founder-Led Sales and Strategic Early Hiring Nathan queries standard startup sales milestones, prompting Richard to emphatically advocate for founder-led sales up to early PMF and advise against prematurely hiring corporate VPs of sales.13:56–19:21 · Nathan pushing back 6/10 Determining ACV Thresholds for Sales Interaction Nathan challenges Richard on the financial viability of touch sales at low ACVs and pushes past non-committal answers regarding expansion quota models. Richard adapts by giving concrete thresholds and splitting quota structures between AMs and CSMs.19:21–20:35 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions Nathan runs through the standard closing rapid-fire format. Richard shares personal background, book habits, and advice on listening to others.

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

0:00 · Nathan 72.9% · guest 27.1%0:00 · Nathan 72.9% · guest 27.1%3:00 · Nathan 16.7% · guest 83.3%3:00 · Nathan 16.7% · guest 83.3%6:00 · Nathan 41.7% · guest 58.3%6:00 · Nathan 41.7% · guest 58.3%9:00 · Nathan 9.7% · guest 90.3%9:00 · Nathan 9.7% · guest 90.3%12:00 · Nathan 22% · guest 78%12:00 · Nathan 22% · guest 78%15:00 · Nathan 25.9% · guest 74.1%15:00 · Nathan 25.9% · guest 74.1%18:00 · Nathan 37.8% · guest 62.2%18:00 · Nathan 37.8% · guest 62.2%21:00 · Nathan 58.4% · guest 41.6%21:00 · Nathan 58.4% · guest 41.6%
Sharpest disagreement ▶ 18:07 Standing Ground on Hybrid Quota Structure

Richard firmly pushes back against Nathan's demand to pick a single side between group and individual quotas, insisting both are required.

 Hardest push from Nathan ▶ 14:26 Refusing Deflection on Sales Unit Economics

Nathan interrupts Richard's tangent on role definitions to refocus the discussion on the exact price floor required for human sales touch.

 Biggest teaching moment ▶ 11:21 Explaining the Founder Sales Advantage

Richard educates early-stage founders on why incoming sales hires cannot match founder close rates due to the unique authority and rapport founders carry.

 Nathan holds their own ▶ 8:04 Benchmarking Gainsight Rep Turnover Metrics

Nathan leverages specific operational metrics from his past interview with Nick Mehta to probe Richard on sales rep quotas and retention benchmarks.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Early Gainsight Engagement and Evolving Training Models 4312 Nathan inquires about Richard's early pricing and training model changes. Richard explains his transition to remote cohort-based reinforcement training, maintaining a friendly, cooperative dynamic.
Client Capacity, Lifestyle Balance, and Book Project 7424 Nathan introduces detailed data points from his previous interview with Gainsight's CEO, asking Richard to dissect where the sales system scales or breaks. Richard outlines why early sales processes must be treated as hypotheses and tested against customer feedback.
Founder-Led Sales and Strategic Early Hiring 4522 Nathan queries standard startup sales milestones, prompting Richard to emphatically advocate for founder-led sales up to early PMF and advise against prematurely hiring corporate VPs of sales.
Determining ACV Thresholds for Sales Interaction 7436 Nathan challenges Richard on the financial viability of touch sales at low ACVs and pushes past non-committal answers regarding expansion quota models. Richard adapts by giving concrete thresholds and splitting quota structures between AMs and CSMs.
The Famous Five Rapid-Fire Questions 2211 Nathan runs through the standard closing rapid-fire format. Richard shares personal background, book habits, and advice on listening to others.

Statements from this episode (12)

What-if
Harris Regrets Declining Gainsight Stock Options In Early Consulting Deal
“You know, the biggest mistake I made in that deal is I should have taken options, but that's, so that is an instance where I got in really early to build.”
Richard Harris May 8, 2021 ▶ 3:16
Disclosure
Harris Charges Flat $18,000 For Five-Week Sales Training Engagements
“Or for something like that, it's around 18, give or take. Yeah. For the five week. And so, and I don't charge by the hour and I don't charge by the head.”
Richard Harris May 8, 2021 ▶ 5:39
Insight
Startup Sales Lack Universal Playbooks During The First Two Years
“Everything's an experiment the first two years in sales, right? There is no, here's the playbook for everybody.”
Richard Harris May 8, 2021 ▶ 8:50
Insight
Startups Must Hire Natural Closers Before Building Formal Sales Processes
“So what I think the key piece is bringing on that closer first. You need to bring in the closer who knows how to do it without the process being built.”
Richard Harris May 8, 2021 ▶ 9:25
Insight
Founders Should Delay Formalizing Sales Processes Until Rep Two Or Three
“Yeah, you do want a sales process, but not super early on, not with your first, second, or third rep. Maybe by the time you get to your second or third, you start to figure out what your first process is. And even then I call it a process hypothesis because it…”
Richard Harris May 8, 2021 ▶ 9:37
Insight
Founders Must Personally Lead Early Sales To Understand Their Motions
“1000% founders need to do the first part of sales. I don't know if it needs to be a number, like a million, like it depends on sort of what the, you know, they need to do it so they can understand the motion at the early stage, right? It's the pre series a or …”
Richard Harris May 8, 2021 ▶ 11:22
Insight
Harris Warns Founders That Hired Reps Rarely Match Their Close Rates
“What founders also have to do is they got to realize that their reps are never going to be able to close at their ratio in most cases, because they're the founder.”
Richard Harris May 8, 2021 ▶ 11:41
Insight
Big-Company Sales VPs Frequently Fail As First Startup Sales Hires
“If I go see people hire VPs of sales from places like Oracle, Or some other big company as their first rep, the biggest challenge, the biggest reason they don't work out is because they haven't actually built something from the bottom up. They haven't built th…”
Richard Harris May 8, 2021 ▶ 13:19
Insight
SaaS Products Need $2,500 Minimum ACV To Justify Human Sales Touch
“I think it's gotta be, I think it's gotta be a couple hundred bucks a month. It's gotta get to 2500 dollars a year for it to be worthy of some level of touch.”
Richard Harris May 8, 2021 ▶ 15:19
Opinion
Customer Success Teams Inherit False Beliefs That Selling Is Inherently Bad
“Part of the challenge with customer success is they've been fault, been fed a false belief system that sales is bad.”
Richard Harris May 8, 2021 ▶ 16:54
Insight
Harris Advises Tying Equity To Quota Goals To Improve Sales Retention
“There should always be a smidge of equity into this goal, right? Like the more you give back to your team and they feel like they have ownership of the organization, The longer they're going to stay”
Richard Harris May 8, 2021 ▶ 18:43
Assertion Not checkable as stated
Statistically Only One In Three Sales Reps Actually Succeeds
“Statistically, I see about one in three reps actually making it on a regular basis.”
Richard Harris May 8, 2021 ▶ 19:15
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