According to GeekWire, Smartsheet has hired former Payscale CEO Scott Torrey as its new chief revenue officer, reuniting him with Concur co-founder and current Smartsheet CEO Rajeev Singh. This continues a leadership shuffle that also recently brought in Pratima Arora as CPO, Ravi Soin as CISO, and Cynthia Tee as CTO. The company, which went private earlier this year in an $8.4 billion deal, generates over $1 billion in annual revenue. In a separate major move, Apple announced it has hired Amar Subramanya, a corporate VP at Microsoft who only joined in July, as its new vice president of AI, where he will lead Apple Foundation Models and report to Craig Federighi. This comes as Apple’s senior VP for AI, John Giannandrea, steps down, and the company works to catch up in the AI race after delaying a new Siri version.
Smartsheet Bets on Familiar Faces
So, Smartsheet is bringing in another old Concur hand. Scott Torrey and Rajeev Singh have a long history, and that’s probably the point. When a private equity firm like Vista Equity Partners takes a company private in a massive $8.4 billion deal, the pressure for predictable, efficient growth is immense. Bringing in a known quantity, someone who already knows the CEO’s playbook from their nearly two decades together at Concur, is a safe bet. It reduces risk in the crucial go-to-market engine. But here’s the thing: is “safe” what Smartsheet needs right now? Singh told the Engage conference it’s time to “step out of the shadows” and shed the “online spreadsheet” perception. That requires bold, transformative thinking, not just executing a familiar sales playbook better. The new Intelligent Work Management platform is a step in that conceptual direction, but selling a grand, AI-powered “platform” is vastly different from selling a productivity tool. Torrey’s challenge won’t just be driving revenue; it’ll be fundamentally changing what Smartsheet’s revenue even represents.
Apple’s Desperate AI Grab?
Now, let’s talk about Apple. Hiring Amar Subramanya is a huge signal. Poaching a top AI researcher who helped lead Gemini at Google, and who was just at Microsoft for a few months, shows Apple is willing to open its checkbook and shake up its culture to get the talent it needs. He’s reporting directly to Craig Federighi, which centralizes AI leadership under software engineering—a pragmatic move. But let’s be skeptical for a second. This feels reactive. John Giannandrea’s retirement, as noted in the official announcement, might have been planned, but the timing alongside a very public Siri delay and perceived AI lag paints a picture of a course correction. Can one hire, no matter how brilliant, reverse that narrative? Apple’s strength has always been vertical integration—making the silicon, the OS, and the apps sing together. Their AI success depends on executing that same playbook flawlessly in a domain where competitors are already on their third or fourth generation models. Subramanya’s job isn’t just research; it’s velocity.
The Bigger Picture: Shuffling Decks
Basically, both stories are about established players trying to reignite growth through executive talent. Smartsheet is doing it under the intense scrutiny of private equity ownership, where the timeline for results is compressed. Apple is doing it under the glaring spotlight of public market and media pressure, where every AI announcement is compared to OpenAI or Google. These aren’t startups bringing in visionary founders; they are large corporations hiring seasoned operators. That tells you the phase these companies are in: execution over pure innovation. The real test for Torrey is whether he can sell a vision, not just a tool. For Subramanya, it’s whether he can inject urgency and openness into Apple’s famously secretive and deliberate development culture. I think both have their work cut out for them.
