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Jul 1, 2019 · 31m · saastr

From Freemium to Enterprise with Slack

Danny Herzberg · 16m spoken Kevin Egan · 12m spoken
0:00 / 0:00
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Slack sales executives Kevin Egan and Danny Herzberg share key go-to-market strategies for scaling a product-led company from organic freemium adoption into large-scale enterprise deployments. Drawing from industry experience at Oracle, Salesforce, HubSpot, and Slack, they detail principles for creating buyer value, structuring sales segmentation, and building cross-functional enterprise readiness.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →

Jason as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Jason pushing back 0.0
05100:0010:0020:0030:005:11–10:51 · Jason as informed peer 0/10 Creating Value vs Extracting Value: The HubSpot Inbound Model Danny delivers a solo keynote presentation detailing HubSpot's inbound marketing strategy, free tools like the Website Grader, and the philosophy of creating value rather than extracting it. With no host participation on stage, interaction scores remain zero.10:52–15:53 · Jason as informed peer 0/10 Slack's Product-Led Growth and Value-Driven Outbound Strategy Danny breaks down Slack's technical buyer persona and product-led growth model, detailing how BDRs synthesize grassroots user feedback to create executive value. The segment is a non-combative conference monologue.15:56–22:55 · Jason as informed peer 0/10 Segmenting Sales Teams and Automating Downmarket Customer Journeys Danny explains Slack's iterative sales segmentation, contrasting the sales-heavy Box model against Atlassian's self-serve model before shifting the SMB team upmarket. The presentation proceeds without host engagement.22:55–30:10 · Jason as informed peer 0/10 Enterprise Readiness, Grid Adoption, and Organizational Commitment Kevin discusses the operational reality of moving upmarket into enterprise accounts like IBM and Oracle, emphasizing that security, compliance, and organizational buy-in are essential. No host interaction occurs during the keynote.30:10–31:22 · Jason as informed peer 0/10 Summary of Takeaways and Session Conclusion Kevin summarizes the three main takeaways around value creation, dynamic segmentation, and company-wide enterprise commitment, closing the keynote smoothly.5:11–10:51 · Guest teaching 0/10 Creating Value vs Extracting Value: The HubSpot Inbound Model Danny delivers a solo keynote presentation detailing HubSpot's inbound marketing strategy, free tools like the Website Grader, and the philosophy of creating value rather than extracting it. With no host participation on stage, interaction scores remain zero.10:52–15:53 · Guest teaching 0/10 Slack's Product-Led Growth and Value-Driven Outbound Strategy Danny breaks down Slack's technical buyer persona and product-led growth model, detailing how BDRs synthesize grassroots user feedback to create executive value. The segment is a non-combative conference monologue.15:56–22:55 · Guest teaching 0/10 Segmenting Sales Teams and Automating Downmarket Customer Journeys Danny explains Slack's iterative sales segmentation, contrasting the sales-heavy Box model against Atlassian's self-serve model before shifting the SMB team upmarket. The presentation proceeds without host engagement.22:55–30:10 · Guest teaching 0/10 Enterprise Readiness, Grid Adoption, and Organizational Commitment Kevin discusses the operational reality of moving upmarket into enterprise accounts like IBM and Oracle, emphasizing that security, compliance, and organizational buy-in are essential. No host interaction occurs during the keynote.30:10–31:22 · Guest teaching 0/10 Summary of Takeaways and Session Conclusion Kevin summarizes the three main takeaways around value creation, dynamic segmentation, and company-wide enterprise commitment, closing the keynote smoothly.5:11–10:51 · Guest disagreement 0/10 Creating Value vs Extracting Value: The HubSpot Inbound Model Danny delivers a solo keynote presentation detailing HubSpot's inbound marketing strategy, free tools like the Website Grader, and the philosophy of creating value rather than extracting it. With no host participation on stage, interaction scores remain zero.10:52–15:53 · Guest disagreement 0/10 Slack's Product-Led Growth and Value-Driven Outbound Strategy Danny breaks down Slack's technical buyer persona and product-led growth model, detailing how BDRs synthesize grassroots user feedback to create executive value. The segment is a non-combative conference monologue.15:56–22:55 · Guest disagreement 0/10 Segmenting Sales Teams and Automating Downmarket Customer Journeys Danny explains Slack's iterative sales segmentation, contrasting the sales-heavy Box model against Atlassian's self-serve model before shifting the SMB team upmarket. The presentation proceeds without host engagement.22:55–30:10 · Guest disagreement 0/10 Enterprise Readiness, Grid Adoption, and Organizational Commitment Kevin discusses the operational reality of moving upmarket into enterprise accounts like IBM and Oracle, emphasizing that security, compliance, and organizational buy-in are essential. No host interaction occurs during the keynote.30:10–31:22 · Guest disagreement 0/10 Summary of Takeaways and Session Conclusion Kevin summarizes the three main takeaways around value creation, dynamic segmentation, and company-wide enterprise commitment, closing the keynote smoothly.5:11–10:51 · Jason pushing back 0/10 Creating Value vs Extracting Value: The HubSpot Inbound Model Danny delivers a solo keynote presentation detailing HubSpot's inbound marketing strategy, free tools like the Website Grader, and the philosophy of creating value rather than extracting it. With no host participation on stage, interaction scores remain zero.10:52–15:53 · Jason pushing back 0/10 Slack's Product-Led Growth and Value-Driven Outbound Strategy Danny breaks down Slack's technical buyer persona and product-led growth model, detailing how BDRs synthesize grassroots user feedback to create executive value. The segment is a non-combative conference monologue.15:56–22:55 · Jason pushing back 0/10 Segmenting Sales Teams and Automating Downmarket Customer Journeys Danny explains Slack's iterative sales segmentation, contrasting the sales-heavy Box model against Atlassian's self-serve model before shifting the SMB team upmarket. The presentation proceeds without host engagement.22:55–30:10 · Jason pushing back 0/10 Enterprise Readiness, Grid Adoption, and Organizational Commitment Kevin discusses the operational reality of moving upmarket into enterprise accounts like IBM and Oracle, emphasizing that security, compliance, and organizational buy-in are essential. No host interaction occurs during the keynote.30:10–31:22 · Jason pushing back 0/10 Summary of Takeaways and Session Conclusion Kevin summarizes the three main takeaways around value creation, dynamic segmentation, and company-wide enterprise commitment, closing the keynote smoothly.

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

0:00 · Jason 0% · guest 100%0:00 · Jason 0% · guest 100%3:00 · Jason 0% · guest 100%3:00 · Jason 0% · guest 100%6:00 · Jason 0% · guest 100%6:00 · Jason 0% · guest 100%9:00 · Jason 0% · guest 100%9:00 · Jason 0% · guest 100%12:00 · Jason 0% · guest 100%12:00 · Jason 0% · guest 100%15:00 · Jason 0% · guest 100%15:00 · Jason 0% · guest 100%18:00 · Jason 0% · guest 100%18:00 · Jason 0% · guest 100%21:00 · Jason 0% · guest 100%21:00 · Jason 0% · guest 100%24:00 · Jason 0% · guest 100%24:00 · Jason 0% · guest 100%27:00 · Jason 0% · guest 100%27:00 · Jason 0% · guest 100%30:00 · Jason 0% · guest 100%30:00 · Jason 0% · guest 100%
Sharpest disagreement ▶ 22:55 Correcting the narrative on Stewart Butterfield's sales quote

Kevin playfully refutes the popular industry myth that Slack's CEO vowed never to hire salespeople, clarifying that the famous quote was taken out of context.

 Hardest push from Jason ▶ 18:00 Questioning static organizational design

Danny pushes back against the standard SaaS approach of setting sales segmentation once and leaving it static, arguing teams must constantly re-evaluate headcount allocation.

 Biggest teaching moment ▶ 5:10 Rethinking sales from extraction to value creation

Danny educates the audience on why standard quota-driven upsell tactics fail in a modern SaaS motion compared to frontloading free value and earning buyer goodwill.

 Jason holds their own ▶ 26:00 Dismantling enterprise freemium misconceptions

Kevin demonstrates deep domain expertise by citing Ben Horowitz and explaining that freemium viral adoption cannot bypass traditional enterprise procurement, security, and politics.
the scores for every segment, with the reasoning behind each
ChapterTopicJason as informed peerGuest teachingGuest disagreementJason pushing backWhy
Creating Value vs Extracting Value: The HubSpot Inbound Model 0000 Danny delivers a solo keynote presentation detailing HubSpot's inbound marketing strategy, free tools like the Website Grader, and the philosophy of creating value rather than extracting it. With no host participation on stage, interaction scores remain zero.
Slack's Product-Led Growth and Value-Driven Outbound Strategy 0000 Danny breaks down Slack's technical buyer persona and product-led growth model, detailing how BDRs synthesize grassroots user feedback to create executive value. The segment is a non-combative conference monologue.
Segmenting Sales Teams and Automating Downmarket Customer Journeys 0000 Danny explains Slack's iterative sales segmentation, contrasting the sales-heavy Box model against Atlassian's self-serve model before shifting the SMB team upmarket. The presentation proceeds without host engagement.
Enterprise Readiness, Grid Adoption, and Organizational Commitment 0000 Kevin discusses the operational reality of moving upmarket into enterprise accounts like IBM and Oracle, emphasizing that security, compliance, and organizational buy-in are essential. No host interaction occurs during the keynote.
Summary of Takeaways and Session Conclusion 0000 Kevin summarizes the three main takeaways around value creation, dynamic segmentation, and company-wide enterprise commitment, closing the keynote smoothly.

Statements from this episode (8)

Opinion
Salesforce's 2002 30-day free trial was its key differentiator against Siebel
“The Salesforce trial was a 30 day trial, up to five users, but the sales rep could toggle it up to 20 users, however many users they wanted, and really put the technology in the hands of the user. And that was like the key differentiator from Siebel at the tim…”
Kevin Egan Jul 1, 2019 ▶ 2:40
Assertion Supported
Dropbox had reached 100 million user signups by 2013
“I joined in 2013, there was a hundred million people that signed up for the, ah, for Dropbox”
Kevin Egan Jul 1, 2019 ▶ 3:52
Assertion Supported
HubSpot required new sales reps to build websites before pitching products
“Literally every sales rep spent two full weeks in a classroom building their own website, understanding what it feels like to be in a small business owner's shoes, and then the sales process would take three, four, up to five calls before you connect the dots …”
Danny Herzberg Jul 1, 2019 ▶ 10:18
Disclosure
Slack's early sales team operated out of Zendesk rather than Salesforce
“Early days we had an accounts team and the accounts team would work out of Zendesk, not Salesforce. So it was almost like an extension of customer support and they would talk to a dentist office and the CIO of a fortune 100 company in the same day.”
Danny Herzberg Jul 1, 2019 ▶ 17:09
Assertion Supported
Box uses sales reps for 25-employee companies while Atlassian uses none
“Box has, I think, a sales team that staffs, even, you know, 25 employee company can talk to a sales rep and engage, and those people are on quota, and that's a full team right there. And then on the extreme, on the other side of the spectrum is Atlassian, whic…”
Danny Herzberg Jul 1, 2019 ▶ 20:22
Disclosure
Slack replaced SMB sales reps with automated onboarding to move upmarket
“What we decided to do was completely shift the SMB team upmarket turn them into a mid-market organization. Work super closely with our counterparts in the product growth team and the marketing team to figure out how do we systematically build the kinds of ques…”
Danny Herzberg Jul 1, 2019 ▶ 21:18
Assertion Supported
IBM was Slack's largest customer with nearly 130,000 daily active users
“So today we have, we count IBM as our largest customer with close to a 130,000 daily active users.”
Kevin Egan Jul 1, 2019 ▶ 26:12
Assertion Supported
Oracle reached approximately 90,000 active users on Slack
“Ah, Oracle is a customer that's reaching about 90,000 active users.”
Kevin Egan Jul 1, 2019 ▶ 26:18
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