Andrew Bennett
Chief Marketing Officer · Go-To-Market Leader
A CMO who has also run a 400+ person global sales organization — brand and revenue held in the same pair of hands.
Profile
Marketing leadership and sales leadership are usually two separate careers. Mine has been both: I built Smartsheet's demand engine and owned it for a decade, ran a 400+ person global commercial sales organization through the 2018 NYSE IPO, then held the CMO seat while revenue grew from $550M to $1B.
That path shapes how I work. I have carried a nine-figure bookings number at a public company, so I know which marketing metrics drive the business outcomes a board actually cares about — and which ones do not.
I was most recently at Elementum, an AI-native company where I inherited one dedicated marketer. I live in Seattle.
Selected work
- Asking Claude to review how I use ClaudeSeptember 2026One open-ended prompt asking Claude to audit seven weeks of my own usage — the scorecard it produced, the gaps it found, and the two structural fixes we shipped in the same session.
- Building this site — the case for ground-level AI fluencyAugust 2026Why I think every marketer needs hands-on AI fluency in 2026, and what it actually took to build this site with an AI coding agent. Still in progress, deliberately.
- Snowflake Summit 26 — making customers the voice of a repositioningJune 2026Elementum's first Summit as a repositioned company — two enterprise customers on Snowflake keynote stages, Product Partner of the Year, and a nomination-only dinner program that ran the week.
- Sponsor X — putting STEM nonprofits on a Formula 1 carMarch 2023A world-first brand program with McLaren Formula 1 that gave Smartsheet's sponsorship inventory away to STEM nonprofits, reaching 55 million viewers at debut.
- Building Smartsheet's GTM engine — PLG before it had a nameJune 2021A decade owning demand generation at Smartsheet — and how reading the self-serve motion's signals let us aim a sales-led motion on top of it, carrying commercial ARR to $550M and the company upmarket.