Glean founder Arvind Jain—don’t wait to go after enterprise accounts

There’s no rule that says B2B startups can only work with small businesses—take it from Arvind Jain, who has been competing for enterprise business since he founded Glean.

Jain founded Glean in 2019 as an AI-powered workplace search engine designed to help employees browse their company apps to find the information they need and boost productivity. Given how quickly company tech stacks can get complicated and siloed, the opportunity for a solution was definitely there. Since then, Glean has raised $155M+ and grown to more than 200 employees while staying true to its initial mission. Jain joined me on the Sit Down Startup podcast to share his experience and provide some key insights for founders just getting started.

Jain, with extensive Silicon Valley experience, including as an engineer at Google, shares valuable insights and strategies for closing enterprise accounts from day one. While starting small often makes a lot of sense, Jain advises against waiting to reach a certain size or maturity level before targeting large businesses.

Ask the hard questions

It’s no surprise with his strong technical background, but Jain underscores the importance of building technically robust and market-ready products from the outset to establish credibility. Every good B2B partnership is a true partnership. Make sure prospective clients are willing and able to implement what you’re offering.

Quantify the problem

Many founders advise ruthlessly prioritizing the business problem you’re solving. Jain advises taking it a step further and proving the value of your product by quantifying the problem your customer base is facing. Lost productivity hours can feel like a fuzzy concept until or unless founders lay out what’s really at stake—internal inefficiencies can have a huge impact on the bottom line, and Jain lays that out for potential customers. Regardless of the problem a startup is solving, enabling sales people (and founders themselves) to quantify the impact of the solution can go a long way.

Sell at the top

It’s common for enterprise companies to assemble buyer groups of cross-functional leaders to evaluate software solutions that meet a range of needs. Given the size and scale of the operation, one solution often has to meet several functional requirements before purse strings, at that level and spend, can open. The CIO isn’t always involved in the discussion from the start. But Jain suggests starting right there at the top: pitching your product to key C-suite leaders like CIOs and letting the word spread internally.