Andy Bailer started as employee number 1,200 at ServiceNow in 2012, just after the IPO. He spent 11 years inside the business, 44 or 45 quarters, as Mike points out, moving through BDR, BDR management, partners and alliances, inside sales, and solution sales before leaving for CDW and eventually Atlassian. He is now Director of Strategic Accounts at Tanium, covering enterprise cybersecurity in the Northeast US.

This conversation covers the full arc: what a decade-plus inside one of the world's fastest-growing enterprise software companies actually teaches you, why the BDR skillset never leaves the best sellers even when they are running seven-figure accounts, and what enterprise buyers in cybersecurity are actually thinking when they go quiet on you.

What's covered:

• Why staying at one company through three distinct growth phases gives you something job-hopping cannot
• The hardest career transition Andy made — and why it was IC to manager, not any of the others
• What strategic account management actually means at Tanium versus what the title implies
• How CISOs buy: not on fear, but on trust and proof
• Why silence from a buyer is not progress — and what to do about it
• Multi-threading as a discipline, not a tactic
• The BDR habit Andy still uses every Monday morning, 12 years on
• Pipeline coverage as a vanity metric: why 3X unqualified beats 1.5X quality every time (it does not)
• The Challenger Sale, the Enneagram, and what Andy learned about his own selling style

About Andy Bailer:

Andy Bailer is Director of Strategic Accounts at Tanium, where he covers enterprise cybersecurity accounts across the Northeast US. He spent 11 years at ServiceNow across BDR, management, partners and alliances, inside sales, and solution sales roles, before positions at CDW and Atlassian. He is based in the US.

Links:
The Outside Seat website: theoutsideseat.com
InsideNow: insidenow.io
Andy Bailer on LinkedIn: https://www.linkedin.com/in/andrewbailer/

The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week.

Episode 6 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a-sales-exec/

InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io