Why private equity paid $8.4B for Smartsheet

Praerit Garg, President of Innovation, Products, and Tech at Smartsheet, shares invaluable insights into scaling SaaS businesses, transitioning from SMB to enterprise, and the transformative role of AI in work management. With an illustrious career spanning Microsoft, AWS, and Smartsheet, Garg delves into the nuances of product-led growth (PLG), the importance of customer-centric product management, and lessons from taking a company public.

The Smartsheet story: From startups to enterprises

Smartsheet, a leading work management platform, caters to businesses of all sizes, from boutique firms to industry giants.

“The biggest challenge—and opportunity—when serving both SMBs and enterprises is delivering a unified experience,” says Garg.

“A small business owner running a boutique firm expects the same level of reliability as a Fortune 500 enterprise managing thousands of projects. The key is to design a product that scales both in complexity and simplicity, without alienating either segment.”

He emphasises the importance of structuring the product organisation around core personas—the work manager, the enterprise portfolio manager, and the collaborator—ensuring tailored solutions for each. “We wake up every morning asking: ‘How do we make their lives easier?’ That’s the North Star for our product teams.”

Scaling up: Moving from SMB to enterprise

For SaaS startups looking to move upmarket, Garg underscores the magic of product innovation. Smartsheet’s journey from an SMB-focused PLG model to enterprise sales was driven by identifying specific pain points faced by large customers.

“When I joined Smartsheet, I asked what was the pivotal moment that propelled the company to IPO. The answer wasn’t just growth—it was a singular insight: enterprise customers needed a way to scale work management consistently across their organisations,” he shares. “We built the Control Center, a capability that allowed teams to manage projects at scale with standardisation and automation. That wasn’t just a feature—it was a game-changing value proposition.”

He advises SaaS founders eyeing enterprise customers to spend at least 30–40% of their time engaging directly with customers. “A great product manager isn’t a feature factory; they’re an investigative journalist, uncovering hidden problems customers didn’t even articulate yet.”

Navigating IPO and the private equity transition

Smartsheet went public in 2018, a milestone that came with both opportunities and challenges. Garg reflects on the disciplined execution required in public markets and the benefits of returning to private equity ownership.

“The public markets demand predictability, but true transformation isn’t predictable—it’s disruptive. When you need to make fundamental shifts, like restructuring teams or evolving GTM strategies, the private markets give you that runway,” he notes. “That’s why going private has been liberating. We’re playing a long game now, not just managing quarterly expectations.”

AI: The game-changer for work management

Artificial intelligence has been a major inflection point for Smartsheet. Garg describes AI as a “once-in-a-generation unlock” for work managers, enabling automation and reducing cognitive load for non-technical users.

“We have to rethink work itself,” he explains. “Today, people spend an incredible amount of time on ‘meta-work’—setting up dashboards, writing formulas, analysing risks. AI eliminates that burden, so work managers can focus on strategy instead of administration.”

He outlines a phased approach to AI adoption, moving from on-demand AI assistance to proactive recommendations and eventually autonomous work management. “First, AI assists. Then, it suggests. Finally, it acts. The goal isn’t just efficiency—it’s about enabling human creativity and decision-making.”

Advice for SaaS founders: Product, pricing, and perseverance

For early-stage SaaS entrepreneurs, Garg shares specific insights from his journey:

1. Deep customer engagement is non-negotiable: “If you're a SaaS business, you earn your customers’ business every day, every hour. If you’re not spending 30–40% of your time talking to real customers or your go-to-market team that talks to customers, you’re not really doing product management.”

2. Product-market fit for enterprise is intentional: “At Smartsheet, enterprise penetration accelerated when we identified a recurring pattern—portfolio managers were manually creating hundreds of project templates. That insight led us to build the Control Center, which unlocked enterprise adoption.”

3. Pricing is a powerful lever: “At AWS, we mastered the art of pricing. The secret? Find the magic metric that customers associate with value, make it easy to get started, and then scale pricing with usage. Smartsheet follows the same principle—start simple, then expand as customers grow.”

4. Leadership is about perseverance: “Startups are incredibly hard. You have to chase your customers, not wait for them to find you. In my first startup, I spent weeks cold-calling customers and driving to their offices to validate our idea. That hustle makes all the difference.”

Final takeaways

Reflecting on his experiences at Microsoft, Amazon, and Smartsheet, Garg emphasises the importance of staying hungry and constantly innovating.

“Microsoft lost its edge when it became inward-looking. Satya [Nadella] changed that by making the company customer-obsessed again. Amazon, on the other hand, was always relentless—that’s its DNA,” he notes.

His final piece of wisdom? “If you have the right people and the right business problem, technology will follow. Build great teams, stay close to customers, and never lose your hunger. That’s how you scale.”

Timestamps

00:00 - Introduction

01:28 - Praerit Garg’s career journey: From Microsoft → AWS → Smartsheet

04:46 - What is Smartsheet? How It serves SMBs & enterprises

07:11 - The land & expand strategy: How Smartsheet scaled enterprise deals

10:27 - Finding the ‘magic metric’ that drives SaaS growth

12:55 - Smartsheet’s IPO journey & why it later went private again

15:37 - AI’s role in work automation & how Smartsheet uses it

21:03 - The enterprise AI trust challenge: Why big companies are cautious

24:58 - What VCs look for in AI SaaS startups

36:30 - Why learning from non-customers unlocks new market opportunities

43:00 - Closing thoughts