In this conversation, Peeyush Upadhyay, Managing Partner at Pekamiar, sits down with Tiffany Chandra, Vice President and Head of Talent Network at Sapphire Ventures.
Tiff explains why one of the most costly mistakes founders make is indexing solely on the logo on a resume, and why the real question is always whether it was the logo or what the person actually did. Why a leader who took a lesser-known company through a tough market can be a better hire than one from a hypergrowth darling. Why a VP of sales who built a hundred-person team at a big company can feel almost paralyzed walking into a team of five.
On AI fluency, she is direct. There is no way around it, only through it, and leaders who ask their teams to get fluent without leading by example will eventually be exposed. She shares how she tests for real fluency by going deeper into what someone built and why, and why companies should not mandate AI for its own sake but start with their most stubborn problem and work backwards.
She walks through the roles being reshaped right now, from RevOps becoming a baby COO at the centre of the business, to why SDRs and BDRs are here to stay at companies like Clay but are now far more consultative and precise. She also describes the war for the top hundred enterprise AEs being pulled toward AI-native companies.
When a startup is competing with a frontier lab or a hyperscaler for elite talent, her answer is that there is no silver-bullet pitch. Founders have to recruit through the entire process, understand what truly motivates each person, and remember that as founders, they have to be recruiters.
She also gets into what derails new executives, from missing context to leaning on an old playbook, why critical roles sit open for months behind generic job descriptions, why leadership churn is the human capital red flag she cannot ignore, and how Sapphire’s talent team is measured on CEO satisfaction rather than placements.
This episode is part of our series on The Scaleup Flight featuring the talent leaders inside VC funds. The people who watch hiring play out across an entire portfolio, and whose knowledge almost never gets written down anywhere.
00:00 Highlights
01:59 Meet Tiffany Chandra
03:11 Welcome, and Sapphire’s growth-stage focus
04:13 Tiff’s role: advisory versus execution
06:20 Working alongside a portfolio company’s talent team
07:45 Sapphire’s two-person talent team and its AI partners
09:15 Scaling past $10M: who gets you to $100M
11:04 Experienced operators versus rising stars
13:25 Letting founders learn from people who have done it
13:55 The costliest mistake: indexing on the logo
16:50 Big-company VPs in five-person teams
17:33 What made you successful two years ago no longer works
19:34 The talent leader as aggregator
19:58 AI fluency: no way around it, only through it
22:40 Who owns AI adoption in the portfolio
25:00 Don’t mandate AI, start with the problem
26:05 How to test AI fluency in an interview
29:15 RevOps becomes the baby COO
32:30 Are SDRs and BDRs here to stay?
35:16 Sales comp and the war for top enterprise AEs
37:50 Winning elite talent against frontier labs
41:29 When executive hires don’t work out
44:30 Early signals a new leader will struggle
46:20 Why critical roles sit open for months
49:30 Talent in Sapphire’s investment diligence
50:35 The red flag: churn at the top
52:56 How Sapphire’s talent team is measured
58:15 What keeps her up at night
59:40 Rapid fire
1:01:21 The hire she still thinks about
1:02:35 Wrap-up
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