A Slack Story Podcast

Money as MacGuffin: Playing the Tech Lottery Game James 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...

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 ratio...

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”), th...

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 servin...

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 wit...

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...

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 th...

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...

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...

Returning to Slack YVR: A Journey Home James Sherrett recounts his return to Vancouver and Slack YVR on Canada Day, 2017. Slack YVR is familiar yet changed, with growth from 1 to 3 floors. We spend some time on the exceptional team that made Slack special, the culture, shared mission, and collaboration that fostered excellence within Slack. Key employees advanced within the company. How Slack YVR...

Discovering Executive Programs by Doing Executive Programs After 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...

Reflections on an Irish Adventure: Transitions and Changes at Slack James Sherrett shares his experience working at Slack and living in Ireland from 2015 to 2017, highlighting both personal and societal changes. He observes Ireland's transformation with the legalization of same-sex marriage and a movement to repeal the abortion ban. He shares his family's daily life while he worked at Slack Dublin...

Values of the Slack Product: Part 2 In 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 f...

Exploring the Values of the Slack Product: Part One In this episode, James Sherrett delves into the starting values of the Slack product and how those values evolved over time. With personal anecdotes and a model of technology from Ursula Franklin's The real World of Technology, James focuses on 3 values of "the system of Slack": default to trust and openness, a shared reality and compassion throu...

A True Irish Coffee Experience — Reviving an Authentic Tradition In 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 hom...

Building Slack's Success in Europe: Leadership Transition & Expansion James Sherrett recounts his experience establishing Slack's EMEA offices in Dublin and London. He reflects on his journey, which included recruiting and training his team, finding new office spaces, and scaling the business from 30 to 120 employees. Sherrett focuses on the leadership transition, detailing his meetings with prosp...

Building Slack London: Growth, Challenges, and Lessons Learned In 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 fie...

Slack's European Expansion Mission James Sherrett narrates the journey to various European cities, from Dublin to London, Paris, and beyond, to promote and expand Slack. He details the challenges and successes of targeting tech-forward organizations, adapting to the unique nuances of over 20 smaller markets, and overcoming skepticism towards new, US technology. Sherrett emphasizes the importance o...

Teenage Years of Slack and Finding a Sales Leader In 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...

Growing Pains at Slack: Embracing Sales and Scaling Up James Sherrett narrates Slack's realization we needed to grow up. But what did that mean? And how did we scale up our sales organization to match the increasingly complex demands of larger customers without losing what made the experience excellent for customers. Sherrett recalls some of challenges faced, solutions implemented, and pivotal dec...

A Dublin Office Halloween: Slack's Journey with Stewart Butterfield Slack'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...

Building Slack Dublin from People James Sherrett recounts his experience of building Slack's team in Dublin from three to 62 employees over 27 months. The journey involved adapting recruitment strategies, localizing the hiring process, and selling Slack to prospective employees alongside customers. Sherrett highlights the initial successes and subsequent challenges in hiring the right talent, incl...

0:38 — The Official Photo and Slack launch event at Trinity College Dublin 1:22 — Meeting the Irish Prime Minister, cultural observations 2:32 — Media questions: jobs, hiring, and Ireland’s expectations 3:01 — The importance of PR and community in Slack’s early success 3:30 — Expanding the story for a broader audience, tech status in Europe 4:52 — Slack’s recognition in different cities and challe...

Introduction: Moving to Dublin, settling in, and the challenge of starting over. 00:30 — Adjusting to a new city: Finding housing, coffee shops, and routines. 00:54 — Working from the Guinness Storehouse, feeling like a traveler. 01:21 — Balancing old and new: Letting go of Vancouver responsibilities, focusing on Dublin. 01:41 — "Culture Carrier" role: What it means and why it matters to a new off...

Boom Times, Not Boom Times Arriving 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 inf...