Raj Singh’s Unexpected Leap: The New Chapter at Smartsheet

When news broke that Rajeev “Raj” Singh would become Smartsheet’s new CEO, a ripple of surprise spread through Seattle’s tech community—and for good reason. Singh’s career has been defined by building enterprise software companies from the ground up, most notably as co-founder of Concur and more recently as CEO of Accolade, which he guided through both IPO and acquisition. Taking the helm of a 20-year-old established company like Smartsheet seemed an unexpected turn for an entrepreneur known for building from scratch. But as Singh explains, this decision represents a fascinating convergence of opportunity, timing, and personal connection that makes perfect sense when you look beneath the surface. “I won’t work at a company that I don’t believe has the capacity to build a great product,” Singh emphasized, pointing to what he calls Smartsheet’s “exceptional bones”—a Seattle tech cornerstone with over $1 billion in revenue, a substantial customer base of major businesses, and significant room for growth in enterprise work management. The company’s headquarters’ location across from Concur in Bellevue adds a poetic touch to this new chapter, creating a physical bridge between his foundational work and this new opportunity.

The AI revolution represents the centerpiece of what drew Singh to Smartsheet at this particular moment. He sees established companies with existing customers, integrated workflows, and rich data as uniquely positioned to implement AI in ways that deliver tangible business value. “The opportunity to get my hands on the wheel of a company that I think can have an incredibly tangible impact on business with AI just seemed like a lot of fun,” Singh shared with characteristic enthusiasm. This perspective challenges the conventional wisdom that AI disruption will primarily come from new startups rather than incumbents. Singh believes Smartsheet’s position—with its deep integration into how thousands of companies manage their work—creates an exceptional foundation for meaningful AI implementation that can transform how businesses operate. His product-focused leadership style aligns perfectly with this vision, as he sees the genuine “love and affinity” users have for Smartsheet as evidence of its potential to evolve into something even more essential to enterprise operations.

Beyond business opportunity, Singh’s decision reflects something profoundly human: the desire to work alongside people he deeply respects and enjoys. His longstanding admiration for former CEO Mark Mader and the chance to partner again with Sunny Gupta, Smartsheet’s executive chair, proved irresistible. Singh and Gupta’s history includes their time at Apptio, where Gupta served as CEO while Singh sat on the board before IBM’s $4.6 billion acquisition in 2023. Now at Smartsheet, they’re “flipping the script” on their previous dynamic, with Singh taking the CEO role while Gupta serves as executive chair. “I want to work with people that I love,” Singh stated plainly, highlighting how personal connections often drive the most significant career decisions. This collaborative partnership comes at a crucial time as Smartsheet navigates an increasingly competitive landscape against both established players like Microsoft, Google, and Salesforce, and newer rivals such as Asana, Monday.com, Airtable, and ClickUp.

Singh’s leadership begins less than a year after Smartsheet went private through an $8.4 billion acquisition by Vista Equity Partners and Blackstone—a transition that introduces unique pressures and dynamics compared to running a public company. However, Singh appears undaunted, having spent considerable time with board members from both firms and finding them receptive to his vision for Smartsheet’s future. He describes them as “like-minded people” aligned on growing Smartsheet into one of the most important companies in enterprise software. This alignment will be crucial as Singh navigates the company through transformation, including recent layoffs affecting over 120 employees. When asked about these cuts, Singh contextualizes them within the broader business environment: “There are no businesses that don’t need massive transformation right now. Anybody who thinks otherwise is missing the story.” Despite these adjustments, Singh remains bullish on Smartsheet’s trajectory, expecting continued growth in employees, customers, and revenue.

The transformation Singh envisions isn’t just about weathering industry changes—it’s about positioning Smartsheet to lead them. His track record suggests he has the experience to navigate this challenge. At Concur, he helped build what became an $8.3 billion acquisition by SAP in 2014, and at Accolade, he guided the health benefits technology company through both public offering and eventual acquisition. This experience with full business lifecycles gives him valuable perspective on Smartsheet’s current position and potential future. Singh sees the company’s existing customer relationships and data as critical advantages in implementing AI solutions that deliver real business value—a perspective that challenges the notion that only AI-native startups will succeed in this new landscape. His vision suggests that established platforms with deep integration into how businesses actually operate may have the edge in creating AI implementations that truly transform work.

Throughout his career, Singh has cultivated lasting partnerships that have defined his success, most notably with Mike Hilton, his longtime friend and business partner who co-founded Concur with Singh and his brother Steve back in 1993, and later joined Singh at Accolade. When asked if Hilton might join him at Smartsheet, Singh laughed but acknowledged the importance of their connection: “Trust me when I tell you, I’ve spent a lot of time talking to Mike about this opportunity and getting his advice… Whether I can lure him away… I don’t know, but I promise you this, he’ll be a wise counsel and a dear friend through the entire process.” This moment reveals something essential about Singh’s leadership approach—he values trusted relationships and collaborative thinking, even as he steps into new territory. As Smartsheet faces the dual challenges of private equity ownership and an increasingly competitive market transformed by AI, Singh’s blend of entrepreneurial vision, product focus, and relationship-centered leadership may be exactly what the company needs to write its next chapter of growth and innovation in the evolving landscape of enterprise work management.