A Slack Story Podcast

Money as MacGuffin: Playing the Tech Lottery GameJames Sherrett reflects on a career largely shaped by the “tech lottery game” of compensation: salary plus stock options. He spent his early work years in late-1990s online finance media, then in roles helping companies adapt to the internet, then six years running a startup that failed. What did he learn? He declines to disclose his Slack earnings. A number is less interesting than understanding how the game works. Then he describes how outcomes of the Tech Lottery Game vary based on factors like teammates, investors, fundraising strength, and especially cap tables (share counts, ownership distribution, liquidation preferences, and complex clauses). He compares Slack’s cap table and $27.7B Salesforce acquisition with Mobify’s tangled cap table. He concludes that money is a startup “MacGuffin.” Day-to-day motivation came from teammates, customers, and doing quality work.00:00 Money And startups01:25 Salary plus options02:15 No upside to sharing numbers03:29 Learning the Tech Lottery Game05:09 Spotting rocket ships06:07 Cap table basics08:06 Comparing two acquisition outcomes09:23 Champagne Problems10:53 Money as MacGuffin12:43 What really motivates14:50 Thank you very much This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Thank You Slack: Seven Years From Employee #9 to a Global CompanyJames Sherrett reflects on leaving Slack on June 5, 2020, exactly seven years after joining as the ninth employee, during which Slack grew from $0 revenue and eight employees to over 2,200 employees in 16 offices and nearly $1B in revenue as a NYSE-listed company. He recounts early marketing and positioning work (“Be less busy”), the 2013 invite launch that drew 8,000 signups in 24 hours, early customer development and support, and the shift into account management and the 2014 paid launch with credits, invoicing, and the “Fair Billing Policy.” He describes building teams, opening Slack’s EMEA office in Dublin in 2015, and later leading Executive Briefing Centres and Innovation Tours. He leaves to prioritize the rest of his life, pursuing advisory work, writing, personal projects, and volunteering.00:00 A farewell to Slack02:06 Why I had to leave04:22 Thank You, Slack letter05:36 Joining as marketer06:49 Positioning Be less busy07:55 Launch day signups09:00 Customer feedback loop14:00 Saying No Nicely17:35 Account Management begins17:55 Paid launch and billing20:35 Offsite, swag and scale22:44 Enterprise sales emerges25:00 Building the Dublin office28:54 Culture and hiring in EMEA32:39 Scaling EMEA sales34:35 Executive Briefing Centers35:52 Innovation Tours program38:35 Gratitude and next chapter41:35 Final reflections and farewell This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Going Public from Yellowstone: Slack’s NYSE Debut and the Reality of ChangeJames Sherrett recounts Slack’s direct public offering (DPO) on June 20, 2019, when shares began trading on the New York Stock Exchange under the ticker WORK, roughly five years after Slack’s first revenue and at a valuation north of $20 billion. Instead of being in New York, he was on a family trip in West Yellowstone with spotty internet, balancing work with family. He describes placing insider sell orders the night before, the DPO mechanics versus an IPO (including immediate insider trading flexibility but greater pricing uncertainty), and a launch-morning panic when his orders hadn’t saved. After spending the day offline biking and exploring with his son, he later catches up on headlines and teammate photos from the NYSE. Sherrett shares Butterfield’s framing of going public as a rite of passage rather than the journey’s peak, then reflects on questions he later received about whether money changed Slack, noting it did through growth, new people, increased conservatism, and intensified competition (especially with Microsoft Teams), while much of Slack’s spirit and customer focus remained. He concludes that the changes weren’t all positive but were overwhelmingly so from his perspective, and teases future stories about finding frontiers, and accepting less ambition.00:00 Slack goes public as WORK01:28 Choosing Yellowstone over the NYSE: family, FOMO, and the trip out03:28 The night before: placing orders and feeling the stakes04:13 DPO vs IPO: why Slack took the direct listing route06:09 Launch morning panic: scrambling and the opening bell07:13 Wall Street movie moment: how the price of WORK got set08:51 Unreal meets reality: orders fill and WORK starts trading10:06 Offline celebration: bikes, rivers, and a day away from the news13:03 Did money change Slack?15:47 Closing thoughts: next on the journey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Harnessing Innovation: Slack's Journey to Innovation ToursJames Sherrett narrates the journey of how Slack capitalized on the rising demand for Innovation Tours, turning it into a valuable business opportunity. Initially uncertain about the concept, Slack learned that Innovation Tours vary greatly, with companies, government agencies, consulting firms, and specialized tour companies organizing them. By assessing the benefits of these tours through a decision matrix, Slack hosted tailored visits, sharing their company culture and innovative practices. These tours increased visibility and led to significant business deals. Ultimately, the Innovation Tours fostered collaboration and showcased Slack as a leader in enabling organizational change.00:00 Introduction: A Slack Story by James Sherrett00:19 The concept of Innovation Tours00:54 Understanding the demand for Innovation Tours01:48 Different types of Innovation Tours03:26 The value of Innovation Tours?05:19 Slack's approach to Innovation Tours06:53 A decision matrix for Innovation Tours09:37 A memorable Innovation Tour experience14:53 Lessons from Building a Culture of Innovation18:37 The Impact of Innovation Tours This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Fumbling Towards Legitimacy: A Senior Technology Strategist at SlackJames Sherrett shares his journey of becoming a Senior Technology Strategist at Slack, a role he describes as initially undefined and nebulous. He recounts how he took on the challenge of defining his new role, like with his previous positions at the company. Sherrett outlines the three primary responsibilities he eventually took on: executive briefing center engagements, investor and partner engagements, and innovation tours. Were there personal and professional hurdles? Some. Frequent travel and the need for self-sufficiency on the road. Sherrett's tries to capture the nuance of becoming 'the Slack man' though he never talked about it. He highlights the importance of presenting a coherent future vision, drawing from experiences and lessons in executive engagement. The episode concludes with a teaser on exploring these executive briefings and the balance between vision and reality.00:00 Introduction: becoming a Senior Technology Strategist01:19 Defining the role: challenges and opportunities02:28 Establishing the hob: Executive Briefings and public speaking03:11 A Portfolio of Activities04:49 Embracing the Slack Man identity06:38 Life on the road and time alone09:40 Changing beliefs and behaviors11:59 Selling the Future: lessons from Microsoft13:36 Conclusion: Working on Slack vision for the future This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Discovering Executive Programs by Doing Executive ProgramsAfter years of team management, James Sherrett finds himself reporting directly to a new, new, new, new boss, Marnie, while no longer managing a team. This transition leads James to explore the world of Executive Programs and Executive Briefing Centres (EBCs), specialized facilities for hosting executives. James learns to adapt to his new role, focusing on building relationships within sales teams, speaking at various industry conferences, and running executive briefing sessions to advance Slack's business goals. Throughout the script, James highlights key strategies, such as thorough preparation for meetings and public speaking engagements, and emphasizes the importance of learning by doing, illustrating his journey from Dublin to various global cities to advance Slack's outreach and impact.00:05 New boss, new role: adjusting to changes02:02 Embracing the essentials and finding core responsibilities02:59 A tour through Executive Programs07:29 Public speaking and representing Slack09:49 The pickle of setting: work and location not aligning15:08 Learning by coing: leading EBCs in London17:50 Conclusion: returning to Vancouver This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Values of the Slack Product: Part 2In this episode, James Sherrett tells the story of Slack's journey in launching the Enterprise Grid product. Through a metaphor inspired by Lego platform sheets, Stewart Butterfield, Slack's co-founder, envisioned connecting multiple Slack workspaces to form an interlinked network. The episode explores the motivations behind this new product, including demands from existing and prospective large customers as well as Slack's own growth needs. Sherrett highlights the challenges and changes faced by Slack in appealing to 'BigCos,' such as increased security features and compliance requirements. This shift involved balancing Slack’s original values with those required by large enterprises, ultimately transforming Slack's product offerings and positioning it for substantial growth.00:00 Introduction to Slack's Enterprise Journey00:29 The metaphor of Enterprise Grid01:32 Challenges with large customers05:43 Prospective customer needs08:33 Slack's needs and market strategy10:22 The launch of Enterprise Grid11:54 Values and technological shifts14:05 Holistic vs. Prescriptive technologies17:12 The impact of Enterprise Grid on Slack18:53 Conclusion and future outlook This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

A True Irish Coffee Experience — Reviving an Authentic TraditionIn this episode, James Sherrett recounts his first Christmas in Ireland, some family traditions and a memorable encounter with Irish neighbors. After being invited for a holiday drink, we discovered the true essence of Irish coffee, a far cry from the mediocre versions previously known. We leave with a deliciously rich and savory homemade Irish coffee recipe. We repatriate the recipe to Canada and it becomes a tradition for family and friends. The episode concludes with the Irish coffee recipe and a cautionary note on moderation.00:00 Introduction: A Irish Irish coffee tale00:18 Settling into Irish life01:20 Meeting the beighbors03:35 A memorable afternoon04:43 The perfect Irish Irish coffee recipe07:07 Serving recommendations This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Building Slack London: Growth, Challenges, and Lessons LearnedIn this episode, James Sherrett narrates the story of establishing Slack's London office, detailing the company's strategic growth and the beginning of its Customer Success practices. Starting with the first hire, Rav Daliwhal, James recounts the early challenges of locating suitable London office space and adapting to the emerging field of customer success. The narrative explores the evolving complexity of Slack's sales teams, reflecting on the company's gentrification and organizational changes. Significant customer acquisitions, office expansions, and the shift from a startup mentality to a structured enterprise come up. James also shares personal insights about the mistakes he made during this growth phase, shedding light on changes in hiring practices and the balancing act between retaining Slack's unique culture and striving for growth. The episode concludes with a teaser on prospecting candidates and further developments in Dublin.00:00 Introduction: The Slack London Story Begins00:25 Meeting Rav Dal: The Start of Customer Success02:21 Establishing Slack London: Challenges and Growth02:51 The WeWork Experience: Pros and Cons04:13 Building the Team: New Hires and Roles04:58 Growing Pains: Transitioning to a Sales Team06:25 Major Clients and Customization08:37 Office Expansion: Moving to Ying House12:50 Reflections on Leadership and Hiring Mistakes21:58 Conclusion: Embracing Change and Growth This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Teenage Years of Slack and Finding a Sales LeaderIn this episode, James Sherrett narrates the journey of Slack in its formative years, focusing on the challenge of hiring a VP of Sales. As the company moved beyond its development-driven roots, it realized the need for an experienced leader who could steer the Sales strategy. Despite internal skepticism about Sales, the team embarked on a rigorous interview process, eventually landing on a top 1 candidate, Bob Frati. Bob's readiness to learn and adapt made him a strong fit, and marked a key turning point in Slack's strategy to scale up its Sales functions. This episode is full of the growing pains and excitement of evolving from a startup to a larger commercial entity.00:23 The Challenge of Hiring a New Boss01:46 Internal Struggles and Realizations06:12 The Search for the Right Candidate10:19 Interviewing Bob: A Standout Candidate14:47 Bob's Impact and the Future of Slack15:47 Conclusion: Expanding Horizons This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

A Dublin Office Halloween: Slack's Journey with Stewart ButterfieldSlack's had its Dublin office, the first outside the Pacific Time zone. Now Slack CEO, Stewart Butterfield, came calling. Also: Hallowe'en. Also: Callowe'en. We reflect on Stewart's growing role and influence both within and outside Slack, including the 'cult of personality' surrounding him. The story finishes by contrasting Slack's values with those of Salesforce after the acquisition.00:00 Introduction: A Slack Story by James Sherrett00:48 Halloween in Dublin: riding the leprechaun01:25 Preparing for Stewart's visit03:04 All Hands meeting from Dublin06:13 Changes happening for Stewart and Slack's culture08:33 The One Mind theory of startups11:05 Style and substance and sprezzatura13:40 The Salesforce acquisition and cultural mismatch This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

0:38 — The Official Photo and Slack launch event at Trinity College Dublin1:22 — Meeting the Irish Prime Minister, cultural observations2:32 — Media questions: jobs, hiring, and Ireland’s expectations3:01 — The importance of PR and community in Slack’s early success3:30 — Expanding the story for a broader audience, tech status in Europe4:52 — Slack’s recognition in different cities and challenges in Europe5:24 — What is Slack? Shifting the story to employment and growth6:02 — Tech industry size in Dublin, yet battling local skepticism6:49 — Outline of Slack’s European expansion strategy7:16 — Building teams, market groupings, and EMEA offices7:43 — Lessons in global market sizing and Europe’s complexity8:10 — The US market advantage, cultural unity9:02 — Pockets of Slack adoption in Sweden, Lithuania, Russia, UK9:23 — Challenges in less receptive European markets10:13 — Meeting LVMH in Paris, cultural nuances10:49 — Berlin IT conference: demos, user engagement, and presentations12:55 — Frankfurt: learning from German family businesses (Tand)13:09 — Selling to skeptics, Bosch, Volkswagen, and progressivism13:31 — Flashbacks to early Slack days, present challenges13:52 — Helping customers build internal cases for Slack14:12 — Presenting to a secretive client in London14:33 — The Sovereign Military Order of Malta: unique client, no deal14:56 — Realization: being used for a “bake off,” lessons learned15:22 — Lessons: pre-qualify opportunities, know your customer16:24 — Hostility to new software, communication concerns16:47 — Relational tactics: comparing Slack to texting and news alerts17:08 — The Maya principle: recalibrating “most advanced yet acceptable”17:30 — Flailing, finding footing, and sales challenges in EMEA18:09 — Next challenges: hiring expertise to change the leaderboard18:30 — Bonus story: interviewing Ciaran Cheney, Slack’s future office manager19:13 — Ciaran’s hiring, celebration at The Long Hall20:09 — Looking ahead: hiring Irish hybrids, finding and addressing biases This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Boom Times, Not Boom TimesArriving in Ireland, first impressions, and the legacy of the Celtic Tiger.0:31 — The Celtic Tiger era: Irish attitudes toward the boom years and the real estate bust.0:59 — The aftermath: Bank bailouts, national debt, and the business context we found as we moved to Ireland to open Slack’s AMEA HQ.1:22 — Learning Irish business culture: Distrust of wealth and the influence of Catholic history.1:55 — Money and Irish identity: Tension between enthusiasm for success and fear of collapse.2:18 — Reading up: Michael Lewis on the Celtic Tiger and the mythic importance of land ownership.2:42 — The Irish play the field: Land, history, and the new tech-driven boom.3:04 — The new boom: US tech companies, Slack’s role, and Irish identity.3:37 — Rich and poor: Tax avoidance, emigration, and the evolving Irish diaspora.4:30 — A changed Ireland: Return migration, new opportunities, and a maturing economy.5:25 — Dublin’s transformation: Housing shortages, digital nomads, and Slack’s diverse team.6:24 — Irish hidden culture: Home counties, accents, and university traditions.6:54 — Upward mobility: Dublin’s draw, real business, and the flow of venture capital.7:38 — Tech’s impact: 10–20% of Dublin’s workforce in tech, joining a new world.8:02 — Real estate stories: House prices before, during, and after the crash.8:48 — Lingering effects: The Celtic Tiger’s hangover, corporate and personal taxes.9:14 — Taxes in Ireland: High rates, deductions at source, and a sense of shared burden. An automated tax system: No returns for most, a mix of relief and helplessness.10:04 — Playground conversations: Meeting locals, signs of a new boom.11:45 — Exploring Dublin: Buses, the zoo, and the city’s layered history.12:19 — Glimpses of hardship: North side poverty, abandoned buildings, and urban contrasts.12:44 — Dublin in transition: The city’s past and future, setting up the next story.13:20 — Closing: Thank you and a teaser for the next episode. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com