Last week, I had the opportunity to attend my first Smartsheet ENGAGE. The conference opened with a message that was equal parts confession, conviction, and call to arms. On stage less than 30 days into the job, new CEO Rajeev Singh framed his first keynote around a simple proposition: Smartsheet isn’t just speeding up work, it wants to make organizations think faster, with what he called “intelligent velocity.

The subtext was unmistakable: this is a reboot. There’s new ownership, a new executive team, and a CEO whose résumé reads like a case study in driving change and growth, from co-founding Concur and betting early on SaaS to scaling virtual care before 2020 forced everyone online. Singh cast those bets as proof he’s comfortable grabbing the future “with both hands.”

A builder at the helm

Singh’s self-portrait was deliberate: “I like to think of myself as a builder.” The implication for customers and partners: expect pace. He lauded a “strong hand”—a 3,300-person team, a massive user base, 150 million automated workflows per month, and a platform he’s used personally for a dozen years. But he also made clear that strong hands still have to be played well.

From doers to thinkers: reframing the buyer

One of the most interesting subtexts of the keynote was a cultural and commercial pivot: moving from “the doers” to “the thinkers.” Smartsheet’s doers, project managers, PMO leads, ops practitioners, built the company. They’re loyal and deeply engaged. But the next chapter requires winning over “thinkers” in the C-suite, CIOs, CFOs, chief strategy officers, who don’t buy tools; they buy ROI.

Singh didn’t dismiss the builders; he asked them to step “out of the shadows” with Smartsheet, bringing success stories and measurable outcomes to the boardroom. In short: keep empowering the champions, but sell to value owners.

A reset on trust—and pricing

In a rare moment of on-stage candor, Singh acknowledged missteps in last year’s pricing rollout. He called it out plainly (“we made mistakes”), described new loyalty benefits and controls to avoid surprise increases, and framed the change as part of a broader leadership principle: transparency + accountability = trust. It was a necessary olive branch to a community that’s been vocal about pricing and product fit, and a signal that this team plans to engage directly and publicly when it stumbles.

Beyond the AI hype: agents, governance, outcomes

On AI, Singh rejected rainbow-and-unicorns rhetoric. His roadmap:

• Gen 1: Copilots
• Gen 2: Agents that notice and act
• Gen 3: Cross-system collaboration with governance

Crucially, he argued that AI is a tool, not a revenue model. Customers shouldn’t pay “per agent”; they should pay for outcomes, productivity, revenue lift, cost reduction, quality gains. That framing is pointed at “thinkers” who are tired of pilots that never scale and CFOs skeptical of perpetual AI premiums.

Two enterprise realities anchored his pitch:

1. Silos: Microsoft, ServiceNow, Salesforce, Workday, don’t naturally talk to each other (and aren’t always incentivized to).
2. Governance matters: audit trails, privacy, compliance, and CSO/legal buy-in are non-negotiable.

Smartsheet’s answer is Intelligent Work Management: a governed, cross-system layer where people, data, and AI “work in concert,” turning insight into impact at scale.

Speaking to a worried workforce

Singh’s AI narrative was calibrated for the cohort most likely to feel threatened: the operators who keep the machine running. He emphasized “brilliant humans leading a digital workforce of agents,” not replacing them. The promised value is practical: agents that flag risks, reassign tasks, update logs, and maintain dashboards, with human review and control. In other words, AI as a multiplier for the anxious middle, not a pink slip.

A new team, a new operating model

If Singh set the north star, CPO Pratima Arora and CTO Cynthia Tee supplied the scaffolding:

• A four-layer architecture (experience, orchestration, application/Smart Hub, foundation/Knowledge Graph).
• Smart Assist (conversational entry point to create projects, surface insights, and apply actions in context).
• Smart Agents (always-on “coworkers” that monitor, recommend, and execute with auditability).
• Smart Flows and Smart Columns (natural-language automation and in-cell intelligence).
• Smart Hub (central controls for building, deploying, and governing AI with full traceability).
• Near-term proof points: AI Charts, rebuilt Table View (95% of sheets load <3s), dashboard filters coming in January, voice-powered form fill, stronger MFA for all plans, Scenario Planning (private beta → EAP), Portfolios (EAP), and the long-requested Dynamic Dropdowns (live).

The meta-message: this isn’t a one-feature wonder; it’s an operating system for enterprise work, and a leadership team intent on finishing long-requested basics and shipping AI.

The ask: bring Smartsheet into the boardroom

Singh closed with a challenge to customers: help shift the narrative from “isn’t that an online spreadsheet?” to “this is our strategic platform.” Smartsheet will bring executive sponsorship, enterprise services, and pricing that supports expansion; customers should bring their outcomes to the CIO and CFO conversation. It’s an explicit bid to reposition Smartsheet from tactical collaboration to company-wide orchestration.

What to watch next

• ROI storytelling: Expect packaged, out-of-the-box solutions and a customer-led marketplace of agents and use cases—ammunition for the “thinkers.”
• Governed cross-system automation: Integrations that move from “sync” to orchestrated, auditable workflows across Microsoft, Salesforce, ServiceNow, Workday.
• Workforce reassurance: More features that let operators see and control what agents do—building confidence that AI augments rather than replaces.
• Pricing alignment to outcomes: If Singh means it, look for models that reward measurable value, not just seats or bot count.

Bottom line: Smartsheet’s opening keynote was a strategic reframing. With a change-agent CEO, a retooled leadership bench, and a message tuned to both builders and business owners, the company is staking out a future where thinking speed, not just task speed, becomes the competitive edge.

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