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Nov 4, 2021 · 47m · saastr

The Sales Playbook for 2022 with Co-Sell CEO Brendon Cassidy and SaaStr CEO Jason Lemkin

Brendon Cassidy · 32m spoken Jason Lemkin · 9m spoken
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In this comprehensive strategy session, SaaStr CEO Jason Lemkin and Co-Sell CEO Brendon Cassidy break down modern B2B SaaS sales playbooks, addressing executive hiring, compensation structures, and the strategic pivot from decaying automated outbound toward warm referral networks and disciplined narrative control.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 21.8% of the talking time here. How this is scored →

Jason as informed peer 6.2 Guest teaching 3.6 Guest disagreement 1.2 Jason pushing back 2.0
05100:0015:0030:0045:001:44–6:22 · Jason as informed peer 5/10 Sales Compensation and Mitigating Rep Risk Aversion Lemkin opens by inquiring about sales compensation inflation and rep expectations. Cassidy explains that paying top reps exceptional comp serves as proof to attract talent and mitigate rep risk aversion, which Lemkin synthesizes into the benchmark that ten million is the new one million.6:24–12:57 · Jason as informed peer 6/10 Fractional Sales Leadership and Thoughtful Executive Recruiting Lemkin and Cassidy discuss the rise of fractional and interim sales leaders. Cassidy compares an open VP of Sales role to a stale real estate listing, and Lemkin builds on this by discussing market transparency and how interim executives can keep listings fresh.12:58–22:26 · Jason as informed peer 6/10 Nurturing Candidates and Managing Executive Transitions The conversation shifts to executive recruiting and topping incumbent sales leaders. Cassidy shares examples from Gong and Outreach on keeping foundational builders motivated, while Lemkin prompts Cassidy on managing phase transitions and recognizing operational warning signs before flat quarters hit board meetings.22:26–31:19 · Jason as informed peer 8/10 Decaying Outbound Efficacy and the Shift to Referral Selling Cassidy outlines the decaying return on brute-force outbound sequences and touches on reduced dependency on Salesforce. Lemkin demonstrates deep market expertise by correcting the framing around Salesforce, explaining that while Salesforce grew massively, its relative share of cloud market cap halved due to the broader expansion of the SaaS ecosystem.31:21–43:42 · Jason as informed peer 6/10 Leveraging Private Referral Networks and SDR Team Realities Cassidy details CoSell's referral network model and the operational reality that VPs of Sales must stay involved in SDR mechanics. Lemkin reinforces this with his own observation about candidate red flags when prospective sales leaders attempt to delegate outbound immediately.1:44–6:22 · Guest teaching 3/10 Sales Compensation and Mitigating Rep Risk Aversion Lemkin opens by inquiring about sales compensation inflation and rep expectations. Cassidy explains that paying top reps exceptional comp serves as proof to attract talent and mitigate rep risk aversion, which Lemkin synthesizes into the benchmark that ten million is the new one million.6:24–12:57 · Guest teaching 4/10 Fractional Sales Leadership and Thoughtful Executive Recruiting Lemkin and Cassidy discuss the rise of fractional and interim sales leaders. Cassidy compares an open VP of Sales role to a stale real estate listing, and Lemkin builds on this by discussing market transparency and how interim executives can keep listings fresh.12:58–22:26 · Guest teaching 4/10 Nurturing Candidates and Managing Executive Transitions The conversation shifts to executive recruiting and topping incumbent sales leaders. Cassidy shares examples from Gong and Outreach on keeping foundational builders motivated, while Lemkin prompts Cassidy on managing phase transitions and recognizing operational warning signs before flat quarters hit board meetings.22:26–31:19 · Guest teaching 3/10 Decaying Outbound Efficacy and the Shift to Referral Selling Cassidy outlines the decaying return on brute-force outbound sequences and touches on reduced dependency on Salesforce. Lemkin demonstrates deep market expertise by correcting the framing around Salesforce, explaining that while Salesforce grew massively, its relative share of cloud market cap halved due to the broader expansion of the SaaS ecosystem.31:21–43:42 · Guest teaching 4/10 Leveraging Private Referral Networks and SDR Team Realities Cassidy details CoSell's referral network model and the operational reality that VPs of Sales must stay involved in SDR mechanics. Lemkin reinforces this with his own observation about candidate red flags when prospective sales leaders attempt to delegate outbound immediately.1:44–6:22 · Guest disagreement 1/10 Sales Compensation and Mitigating Rep Risk Aversion Lemkin opens by inquiring about sales compensation inflation and rep expectations. Cassidy explains that paying top reps exceptional comp serves as proof to attract talent and mitigate rep risk aversion, which Lemkin synthesizes into the benchmark that ten million is the new one million.6:24–12:57 · Guest disagreement 1/10 Fractional Sales Leadership and Thoughtful Executive Recruiting Lemkin and Cassidy discuss the rise of fractional and interim sales leaders. Cassidy compares an open VP of Sales role to a stale real estate listing, and Lemkin builds on this by discussing market transparency and how interim executives can keep listings fresh.12:58–22:26 · Guest disagreement 1/10 Nurturing Candidates and Managing Executive Transitions The conversation shifts to executive recruiting and topping incumbent sales leaders. Cassidy shares examples from Gong and Outreach on keeping foundational builders motivated, while Lemkin prompts Cassidy on managing phase transitions and recognizing operational warning signs before flat quarters hit board meetings.22:26–31:19 · Guest disagreement 2/10 Decaying Outbound Efficacy and the Shift to Referral Selling Cassidy outlines the decaying return on brute-force outbound sequences and touches on reduced dependency on Salesforce. Lemkin demonstrates deep market expertise by correcting the framing around Salesforce, explaining that while Salesforce grew massively, its relative share of cloud market cap halved due to the broader expansion of the SaaS ecosystem.31:21–43:42 · Guest disagreement 1/10 Leveraging Private Referral Networks and SDR Team Realities Cassidy details CoSell's referral network model and the operational reality that VPs of Sales must stay involved in SDR mechanics. Lemkin reinforces this with his own observation about candidate red flags when prospective sales leaders attempt to delegate outbound immediately.1:44–6:22 · Jason pushing back 1/10 Sales Compensation and Mitigating Rep Risk Aversion Lemkin opens by inquiring about sales compensation inflation and rep expectations. Cassidy explains that paying top reps exceptional comp serves as proof to attract talent and mitigate rep risk aversion, which Lemkin synthesizes into the benchmark that ten million is the new one million.6:24–12:57 · Jason pushing back 1/10 Fractional Sales Leadership and Thoughtful Executive Recruiting Lemkin and Cassidy discuss the rise of fractional and interim sales leaders. Cassidy compares an open VP of Sales role to a stale real estate listing, and Lemkin builds on this by discussing market transparency and how interim executives can keep listings fresh.12:58–22:26 · Jason pushing back 2/10 Nurturing Candidates and Managing Executive Transitions The conversation shifts to executive recruiting and topping incumbent sales leaders. Cassidy shares examples from Gong and Outreach on keeping foundational builders motivated, while Lemkin prompts Cassidy on managing phase transitions and recognizing operational warning signs before flat quarters hit board meetings.22:26–31:19 · Jason pushing back 4/10 Decaying Outbound Efficacy and the Shift to Referral Selling Cassidy outlines the decaying return on brute-force outbound sequences and touches on reduced dependency on Salesforce. Lemkin demonstrates deep market expertise by correcting the framing around Salesforce, explaining that while Salesforce grew massively, its relative share of cloud market cap halved due to the broader expansion of the SaaS ecosystem.31:21–43:42 · Jason pushing back 2/10 Leveraging Private Referral Networks and SDR Team Realities Cassidy details CoSell's referral network model and the operational reality that VPs of Sales must stay involved in SDR mechanics. Lemkin reinforces this with his own observation about candidate red flags when prospective sales leaders attempt to delegate outbound immediately.

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

0:00 · Jason 70.4% · guest 29.6%0:00 · Jason 70.4% · guest 29.6%3:00 · Jason 0% · guest 100%3:00 · Jason 0% · guest 100%6:00 · Jason 29.1% · guest 70.9%6:00 · Jason 29.1% · guest 70.9%9:00 · Jason 16.6% · guest 83.4%9:00 · Jason 16.6% · guest 83.4%12:00 · Jason 26.8% · guest 73.2%12:00 · Jason 26.8% · guest 73.2%15:00 · Jason 19.5% · guest 80.5%15:00 · Jason 19.5% · guest 80.5%18:00 · Jason 14.5% · guest 85.5%18:00 · Jason 14.5% · guest 85.5%21:00 · Jason 23.4% · guest 76.6%21:00 · Jason 23.4% · guest 76.6%24:00 · Jason 16.6% · guest 83.4%24:00 · Jason 16.6% · guest 83.4%27:00 · Jason 50.8% · guest 49.2%27:00 · Jason 50.8% · guest 49.2%30:00 · Jason 7.6% · guest 92.4%30:00 · Jason 7.6% · guest 92.4%33:00 · Jason 3.1% · guest 96.9%33:00 · Jason 3.1% · guest 96.9%36:00 · Jason 22.6% · guest 77.4%36:00 · Jason 22.6% · guest 77.4%39:00 · Jason 18.4% · guest 81.6%39:00 · Jason 18.4% · guest 81.6%42:00 · Jason 14.5% · guest 85.5%42:00 · Jason 14.5% · guest 85.5%45:00 · Jason 15.3% · guest 84.7%45:00 · Jason 15.3% · guest 84.7%
Sharpest disagreement ▶ 24:10 Cassidy rejects mass-produced outbound efficacy

Cassidy strongly dismisses the notion that automated brute-force outreach can scale companies to the finish line, arguing that buyers have grown wise to mass quasi-personalized sequences.

 Hardest push from Jason ▶ 25:25 Lemkin reframes decaying playbooks as additive rather than replacement

Lemkin challenges the binary interpretation of decaying outbound channels, clarifying that founders cannot abandon standard playbooks but must layer on warm referral strategies.

 Biggest teaching moment ▶ 9:45 Cassidy educates on sales leadership network signaling

Cassidy educates Lemkin on the hidden reputational cost of prolonged executive searches, likening open roles to stale real estate listings scrutinized in sales leadership communities like Pavilion.

 Jason holds their own ▶ 27:25 Lemkin breaks down macroeconomic cloud market cap shifts

Lemkin commands the discussion by citing market cap data to reframe Cassidy's observation about Salesforce, explaining how macro cloud expansion diluted Salesforce's category share without shrinking its revenue.
the scores for every segment, with the reasoning behind each
ChapterTopicJason as informed peerGuest teachingGuest disagreementJason pushing backWhy
Sales Compensation and Mitigating Rep Risk Aversion 5311 Lemkin opens by inquiring about sales compensation inflation and rep expectations. Cassidy explains that paying top reps exceptional comp serves as proof to attract talent and mitigate rep risk aversion, which Lemkin synthesizes into the benchmark that ten million is the new one million.
Fractional Sales Leadership and Thoughtful Executive Recruiting 6411 Lemkin and Cassidy discuss the rise of fractional and interim sales leaders. Cassidy compares an open VP of Sales role to a stale real estate listing, and Lemkin builds on this by discussing market transparency and how interim executives can keep listings fresh.
Nurturing Candidates and Managing Executive Transitions 6412 The conversation shifts to executive recruiting and topping incumbent sales leaders. Cassidy shares examples from Gong and Outreach on keeping foundational builders motivated, while Lemkin prompts Cassidy on managing phase transitions and recognizing operational warning signs before flat quarters hit board meetings.
Decaying Outbound Efficacy and the Shift to Referral Selling 8324 Cassidy outlines the decaying return on brute-force outbound sequences and touches on reduced dependency on Salesforce. Lemkin demonstrates deep market expertise by correcting the framing around Salesforce, explaining that while Salesforce grew massively, its relative share of cloud market cap halved due to the broader expansion of the SaaS ecosystem.
Leveraging Private Referral Networks and SDR Team Realities 6412 Cassidy details CoSell's referral network model and the operational reality that VPs of Sales must stay involved in SDR mechanics. Lemkin reinforces this with his own observation about candidate red flags when prospective sales leaders attempt to delegate outbound immediately.

Statements from this episode (10)

Insight
Cassidy: Making top sales reps highest paid employees is net positive
“Having some sales people that just absolutely crush it and are the highest paid paid people in the company is almost all net good, you know, from a, you know, they're probably, you're paying them a lot. Maybe they're even overpaid, but like, You know, that the…”
Brendon Cassidy Nov 4, 2021 ▶ 2:55
Insight
Cassidy: Top sales reps won't join startups without proven high earners
“They're going to be really hard to get a really good sale, you know, salesperson to come in with no proof, right? Like, Hey, can I talk to a salesperson and sort of ask, you know, how much they may, you know, how much they've closed, how much they make. And yo…”
Brendon Cassidy Nov 4, 2021 ▶ 5:36
Insight
Cassidy: Prolonged VP of sales searches become increasingly harder to fill
“The problem is, is I viewed like these sales leadership roles are like sort of listing a house on the market, right? The longer it's on the market, the harder it gets to fill it because, you know, there's more community within the sales leadership community th…”
Brendon Cassidy Nov 4, 2021 ▶ 9:47
Insight
Cassidy: Founders should form informal sales councils before opening executive searches
“If I were a founder looking for a VP of sales right now, I would be, and I didn't, you know, I didn't have, you know, a big network of sales leaders that I knew, or whatever, you know, whatever the terms of the scenario are, like, I would be meeting with peopl…”
Brendon Cassidy Nov 4, 2021 ▶ 11:36
Insight
Cassidy: Early sales leadership's institutional capital is rarely replaceable
“The amount of like, you know, sort of sweat equity and intellectual capital that's been built there with that team is not replaceable most of the time.”
Brendon Cassidy Nov 4, 2021 ▶ 19:01
Insight
Cassidy: Mass-produced outbound emails no longer work as buyers grew wise
“Trying to like inundate the market with just this massive amount of like quasi personalized communication, right? Everyone's wise to it now, and you just can't mass produce that and have success, in my opinion, to expect to succeed all the way to the finish li…”
Brendon Cassidy Nov 4, 2021 ▶ 23:55
Assertion Not checkable as stated
Lemkin: Salesforce's share of total cloud market cap halved in five years
“If you look at revenue or market cap, Salesforce has grown incredibly, right? Almost two hundred billion, but its share of, Total revenue and total market cap is half of what it was five years ago, just because the rest of the cloud got so big, right?”
Jason Lemkin Nov 4, 2021 ▶ 27:31
Insight
Cassidy: Meaningful software products require behavioral change, not incremental gains
“In my experience, most meaningful products that I've worked with or sold, there was a pretty, there was a behavioral change component to it. Right. Like it's not just, Hey, we do X just three percent better than Y.”
Brendon Cassidy Nov 4, 2021 ▶ 31:01
Opinion
Cassidy: EchoSign's early team was much better than LinkedIn's
“The team we had at EchoSign was so much better, by the way, there are some great people on our team at LinkedIn, by the way, phenomenal people that have had great success, but overall the team we had at EchoSign was way better. It was a way better team general…”
Brendon Cassidy Nov 4, 2021 ▶ 41:17
Insight
Cassidy: Sales teams should proactively weaponize product weaknesses in competitive deals
“I think realizing what your, not just what your strengths are, but what your weaknesses are, and then weaponizing that before your competitor exposes it as a liability, right? Taking, why do, why should we lose? Okay, we, if we know why we should lose and why …”
Brendon Cassidy Nov 4, 2021 ▶ 45:20
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