A Slack Story Podcast

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

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

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

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

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