As a new grad, Bill Macaitis asked a departing colleague for their best advice at their last-day lunch. The answer: don’t focus on being employed; focus on being employable. Bill has been acting on it ever since. He taught himself SEO when there were no classes for it, and that skill eventually got him hired at Salesforce. He went on to be CMO of Zendesk through its IPO and CMO of Slack during its hypergrowth years. He was also my boss at Salesforce, and he’s the person I’ve called for career advice ever since. This conversation is about the people behind that run: Benioff taking a meeting from a TV screen in a Hawaiian shirt, Mikkel Svane talking him into “beautifully simple,” and Stewart Butterfield judging restaurants by the valet. Bill also talks about the back channels that opened doors he never knew about, and why he always takes the recruiter’s call. Then he gets practical: the two questions he’d ask in any job interview, and what he’d teach himself if he were 25 today. His answer is how to build and govern teams of AI agents, the SEO of this moment.
00:00 — Introducing Bill Macaitis
01:15 — The advice that shaped his career: Be employable, not employed
03:00 — Teaching himself SEO, from Rotten Tomatoes to Fox Interactive Media
05:15 — Kendall Collins, Clarence So, and bringing B2C DNA to Salesforce
07:45 — Marc Benioff, a Hawaiian shirt, and the “social enterprise” homepage test
10:50 — Data over the HiPPO (highest-paid person’s opinion), with George Hu as an ally
13:10 — Mikkel Svane and “beautifully simple” at Zendesk
15:00 — Back channels: how the people who vouch for you open doors you never see
17:20 — Joining Slack early, and why he always takes the recruiter’s call
19:30 — Stewart Butterfield’s restaurant test: the brand is every micro-experience
21:30 — Hypergrowth at Slack: the week-off DAU bet and protecting culture
23:50 — Fair billing, freemium, and a 10-million-person marketing team
25:50 — Advising AI companies, and what he saw in Turing’s Jonathan Siddharth
28:50 — How to find the right company and make yourself stand out
30:30 — The two questions to ask in any interview: growth and NPS
31:30 — The next SEO: building agentic systems and staying employable
33:00 — Lightning round: The Lord of the Rings and what “Who Got Me Here” means
Andrew Braccia, Richard Jalichandra, Bruce Campbell, Colin Fleming, Adam Greco, Maggie Hott, Mark Jung, Michael Lynch, Brad Morris, Jamie Rosenfield, Bill Shaw, Jonathan Siddharth, Kraig Swensrud, AJ Tennant, Lauren Vaccarello
#1 Be Employable, Not Just Employed: Teach Yourself the Skill Nobody Has Yet
Bill’s first job out of college was at System Software Associates, an early ERP company in Chicago. Whenever someone left, the team took them to the colleague’s last-day lunch, and Bill, the new guy, would ask the person leaving for their best piece of advice. One of them told him: “Don’t overly focus just on being employed. Focus on being employable.” Bill took it literally. When SEO was new and there were no classes for it, he read every forum and went to every conference he could. That skill helped grow Fox Interactive Media into the third-largest network of sites in the world. It’s also part of why Salesforce brought him in, when Marc Benioff wanted to rank number one for “CRM.”
Takeaway: Your job can go away. Your skills can’t. Find the thing nobody in the room knows how to do yet and teach yourself. Bill’s answer for today is learning to build and govern teams of AI agents, the SEO of this moment.
#2 The Back Channels Are Always Running: Be Worth Vouching For
Bill didn’t know his former IGN CEO, Mark Jung, had told a headhunter “this guy really likes you” until the Zendesk role showed up. When he went to Salesforce, Richard Jalichandra, a former IGN colleague, turned out to be friends with Kendall Collins and vouched for him. Slack came through Accel’s talent team. For years, Bill had taken recruiters’ calls even when he was happy where he was, just to ask, “How can I help you out?” When the right opportunity came up, his name surfaced.
Takeaway: Someone is talking about you in a room you’ll never see. Do work people are proud to recommend, take the recruiter’s call when you don’t need it, and help them anyway. Those back channels can define a career.
#3 Ask Two Questions Before You Take the Job
Bill calls your next job one of the biggest decisions of your life. Yet he’s watched people take one because it pays 15% more or is closer to home. If he could ask only two questions in an interview: What’s your year-over-year revenue growth? What’s your net promoter score? If they don’t know what NPS is, that’s not a good sign. If growth is in the triple digits and NPS is in the 80s or 90s, go for it. It’s not fun working for a company whose customers hate the product.
Takeaway: Looking for a job is a full-time job. Back-channel the company as hard as they back-channel you, and pick growth and customer love over a bump in pay.
@ 2024 Who Got Me Here, Inc.
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