A Slack Story Podcast

James Sherrett
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In 2013, I started as #9 on the Slack team. A Slack Story tells the best stories from the 7 years and 5 jobs that followed. The Podcast is those stories in audio form. Plus more to come. Subscribe by RSS with this link: https://api.substack.com/feed/podcast/3721181.rss www.slackstory.com

  1. 2D AGO

    Questions That Remain

    Questions That Remain: Luck, Culture vs People, Leaving Before It’s Time James Sherrett reflects on unresolved questions from A Slack Story: the role of luck in Slack’s and his own success, culture versus people as drivers of performance, and how to leave before it’s time by building a life to move toward. He argues luck is unknowable but significant. He quotes Michael Lewis on success being rationalized and luck creating obligation to the unlucky. He notes Slack benefited from launching at the right moment amid enabling technologies and market conditions. On culture versus people, he rejects a zero-sum framing, describing a reinforcing cycle where great people build culture and culture attracts great people. He recounts growing less motivated by Slack’s scale and achievements, defining new goals largely outside work. He tells a pre-pandemic story that helped with his decision to leave and plan life after Slack. 01:38 Luck in Slack's success 04:26 Luck lessons in life 06:34 Culture versus people is the wrong framing 08:26 People build the flywheel 09:35 Leaving before it's time 10:54 Seeking a life after Slack 12:28 Farewell to all that 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

    13 min

  2. MAR 4

    Thank You, Slack

    Thank You Slack: Seven Years From Employee #9 to a Global Company James 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 Slack 02:06 Why I had to leave 04:22 Thank You, Slack letter 05:36 Joining as marketer 06:49 Positioning Be less busy 07:55 Launch day signups 09:00 Customer feedback loop 14:00 Saying No Nicely 17:35 Account Management begins 17:55 Paid launch and billing 20:35 Offsite, swag and scale 22:44 Enterprise sales emerges 25:00 Building the Dublin office 28:54 Culture and hiring in EMEA 32:39 Scaling EMEA sales 34:35 Executive Briefing Centers 35:52 Innovation Tours program 38:35 Gratitude and next chapter 41:35 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

    43 min

  3. FEB 25

    Stories I Haven’t Told You (Yet)

    Slack Frontiers, Almost Getting PIP’d, and Accepting Less Ambition James Sherrett continues A Slack Story with 3 stories he hadn't told yet. First, how Slack launched its customer conference, Frontiers, starting in 2017 after customers began asking for it. He explains how the conference brought together customers, partners, product, and the Slack team, and how it created business urgency by serving as a deadline, including an on-site executive briefing program by 2019. He shares vivid details from Frontiers and the event’s “Frontiers” name inspiration from a Carl Sagan quote about humanity needing a frontier, noting omitted lines about knowing how to reach “a new world next door.” Second, he recounts a January 2020 warning from his boss, Marnie, that he was trending toward a performance improvement plan. Third, Sherrett reflects on accepting less ambition as he played smaller roles as Slack hired world-class experts to replace functions he initially led. He reframing his trajectory as a generalist pioneer who starts new initiatives until others can do them better. He emphasizes humility, change (“burn the metaphorical boats”), and the value of never underestimating sheer gall. He closes with some thoughts about self-awareness, challenge and selling out to do be the best you possible. 00:00 Intro and Feedback 00:40 Why companies host conferences 01:44 Building Slack Frontiers 03:09 Frontiers moments and meaning 05:11 Almost on a PIP 06:38 Resetting from complacency 07:37 Learning to accept less ambition 10:20 A generalist mindset 12:26 Never underestimate sheer gall 14:06 Finding some self awareness 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

    16 min

  4. FEB 18

    WORK on NYSE

    Going Public from Yellowstone: Slack’s NYSE Debut and the Reality of Change James 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 WORK 01:28 Choosing Yellowstone over the NYSE: family, FOMO, and the trip out 03:28 The night before: placing orders and feeling the stakes 04:13 DPO vs IPO: why Slack took the direct listing route 06:09 Launch morning panic: scrambling and the opening bell 07:13 Wall Street movie moment: how the price of WORK got set 08:51 Unreal meets reality: orders fill and WORK starts trading 10:06 Offline celebration: bikes, rivers, and a day away from the news 13:03 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

    16 min

  5. FEB 11

    New Swag: Pocket Squares / Handkerchief / Head Scarf / Hair Tie / Cravat / Dog Scarf

    The Pocket Square Project: Swag off in all directions In this episode, James Sherrett shares how he created unconventional company swag for Slack. From initial inspiration at Heathrow Airport to collaborating with suppliers and distributing pocket squares as multi-purpose swag, he explores the impact and reception of these stylish silk squares. This off-the-books project showcases the playfulness and high standards Slack aspired to in its executive programs. Sherrett reflects on the innovative culture at Slack, the sense of autonomy, and the joy of injecting a sense of play into his work, all while hinting at future episodes on significant milestones like Slack's public offering. 00:00 Introduction: A Slack Story by James Sherrett 00:05 The birth of the pocket square idea 00:43 Finding the right design 01:51 Partnering with Monsoon Corporate Gifts 02:43 The arrival and reactions 03:24 Covert Marketing operations 04:07 Spreading the pocket squares 06:06 Broader swag strategy 06:55 Standards and challenges 08:50 Conclusion: embracing play and change 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

    10 min

  6. FEB 4

    Innovation Tours

    Harnessing Innovation: Slack's Journey to Innovation Tours James 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 Sherrett 00:19 The concept of Innovation Tours 00:54 Understanding the demand for Innovation Tours 01:48 Different types of Innovation Tours 03:26 The value of Innovation Tours? 05:19 Slack's approach to Innovation Tours 06:53 A decision matrix for Innovation Tours 09:37 A memorable Innovation Tour experience 14:53 Lessons from Building a Culture of Innovation 18:37 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

    22 min

  7. JAN 28

    Briefing the Executives

    Reinventing Meetings: The Power of Effective Executive Briefings James Sherrett discusses some common frustrations with meetings and argues for their potential efficiency when conducted properly. By exploring Slack's approach to transforming meetings into executive briefings, he demonstrates how thoughtful execution can drive business success. He highlights the collaboration between Slack's sales teams, Slack executives, and Slack customers to create effective briefings that help close deals. Key results of Slack's briefing process include a higher win rate for deals and significant contributions to annual contract value. 00:00 Introduction: the dreaded meeting 00:57 The case for effective meetings 01:23 Human nature and meetings 03:31 Steps to better ,eetings 05:04 Reinventing meetings as briefings 05:44 Collaborating with our 3 key groups 08:08 Examples of successful briefings 13:37 Results and reflections 15:33 Conclusion: finding competitive advantages in plain sight 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

    17 min

  8. JAN 21

    Becoming a Senior Technology Strategist

    Fumbling Towards Legitimacy: A Senior Technology Strategist at Slack James 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 Strategist 01:19 Defining the role: challenges and opportunities 02:28 Establishing the hob: Executive Briefings and public speaking 03:11 A Portfolio of Activities 04:49 Embracing the Slack Man identity 06:38 Life on the road and time alone 09:40 Changing beliefs and behaviors 11:59 Selling the Future: lessons from Microsoft 13:36 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

    14 min
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About

In 2013, I started as #9 on the Slack team. A Slack Story tells the best stories from the 7 years and 5 jobs that followed. The Podcast is those stories in audio form. Plus more to come. Subscribe by RSS with this link: https://api.substack.com/feed/podcast/3721181.rss www.slackstory.com

Information

  • Creator
    James Sherrett
  • Years Active
    2025 - 2026
  • Episodes
    60
  • Rating
    Clean
  • Copyright
    © James Sherrett
  • Show Website
    A Slack Story Podcast