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Shishir Mehrotra, CEO of Superhuman, joins NEW ECONOMIES to explain why he renamed a 16-year-old company mid-flight instead of just adding a new label on top, why he built his own board by ranking every past boss he’s ever had instead of chasing famous names, and why the real threat to a legacy SaaS category isn’t a faster competitor but the coordination problem AI agents are about to make bigger, not smaller.
About Superhuman
Superhuman is an AI-native productivity suite built from products including, Grammarly, Superhuman Mail (formerly called Superhuman), Superhuman Docs (formerly Coda), and Superhuman Go, serving over 40 million people and 50,000 organizations worldwide.
During this episode, we also hear the four myths of bundling Shishir learned after his time running YouTube’s failed paid products, why marginal churn contribution, not usage, is the real basis for how bundlers split revenue, and how that same framework now governs how he prices and packages Superhuman’s four products. We get into why he treats a rebrand as a “do no harm” exercise for the existing brand first, the DACI-based ritual (Driver, Approver, Contributor, and Informed) his company uses to kill ad hoc meetings entirely, and why he thinks the SaaS apocalypse thesis has the coordination math backwards.
We close on his “Jeopardy style” critique of most board meetings, why he’d rather ask a departing CEO to shadow him for a week than assume he already knows what’s unique about how he runs his own, and how a decade of hitting inbox zero taught him that the goal was never to answer faster, it was to never touch the same email twice.
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Download the transcript 👇
Timestamps
(0:00) Meet Shishir Mehrotra
(1:50) The Naming Process for Superhuman
(9:45) How Rahul (the original founder of Superhuman) and Shishir Met
(11:28) Launching and Building Coda in 2014
(14:42) Lessons from Reid Hoffman
(17:51) Picking the Right Investors as Partners
(19:49) What Is Bad Capital?
(21:42) The Art of Bundling Products
(31:38) The SaaS Apocalypse
(37:50) What’s Missing from Superhuman’s Bundle
(42:40) Getting to Inbox Zero
(50:15) A Week with Shishir
(54:50) How to Build a Board
(1:00:30) Dream Board Member
Our notes from this conversation
1. Bundles aren’t priced by usage, they’re priced by churn risk.
ESPN and History Channel got nearly identical viewing hours on cable, yet ESPN was paid ~20x more. Shishir’s term for the real driver: marginal churn contribution, how many subscribers would cancel if you pulled that one product. That’s what bundlers were actually pricing, even without a name for it.
2. Renaming a 16-year-old company isn’t mechanical, it’s telling 1,500 people their login just changed.
Google’s rebrand to Alphabet was additive; almost nothing changed for employees. Superhuman was different, a name change, not an addition, so every login and website had to move. Decision to roll out: ~4 months.
3. Pick a board member the way you’d pick a boss.
Shishir and his co-founder listed every past boss they’d ever had, 12–15 people, and ranked by who got the best work out of them, not who they liked most.
4. AI agents don’t kill SaaS demand, they multiply the coordination problem.
You don’t need a CRM because you have 10 humans selling; you need it to coordinate them. Swap in 100 virtual sellers and that coordination problem gets harder. His take on usage-based pricing: it’s less philosophy, more workaround, nobody knows how to price a “virtual seat” yet.
5. Inbox zero isn’t about answering fast. It’s about never touching an email twice.
Auto-labels sort mail into ~10 “piles”: inbox, recruiting, customers, media, each handled at a different cadence. Borrowing from Intercom’s Des Traynor: your inbox is what others think you should work on, your to-do list is what you think you should work on, your calendar is what you actually work on. The job is making those three match.
6. The best bundles minimize super-fan overlap, not maximize it.
Most founders assume a bundle should serve one audience deeply. Shishir’s thoughts: you want each product pulling in a different audience, Superhuman Mail skews sales/recruiting, Grammarly skews writers and students, so the bundle expands reach instead of just deepening engagement with the same crowd.
7. Casual fans, not super fans, are where bundles create value.
A la carte pricing only captures people who both want a product enough to pay full price and have the energy to go find it, super fans. Bundling unlocks everyone else: people who wouldn’t have sought the product out alone but will use it once it’s already there.
8. Good investors act like long-term teammates. Bad ones act like bankers.
Shishir’s litmus test: how does an investor behave when a company has to make a short-term-costly, long-term-right call? Reference-check by talking to people who worked with them for years, not just a call or two, the pattern only shows up under real pressure.
Links
Follow Ollie on X: https://x.com/ollieforsyth
Follow Shishir on X: https://x.com/shishirmehrotra
Discover Superhuman: https://superhuman.com
Partners for today’s episode:
Harmonic: Your go-to startup database: https://harmonic.ai
Hostinger: A go-to tool for builders: https://hostinger.com/neweconomies
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