Sean Jacobsohn tests the seller before backing the company. The Norwest partner makes a CEO’s sales ability part of his investment process, placing leadership performance beside product, market, and revenue as a core question. For enterprise software founders, a compelling pitch is only the opening act.
Jacobsohn’s approach comes from experience inside the companies he now evaluates. He worked at HR software startups before investing in them, holding senior roles at WageWorks and Cornerstone OnDemand as both businesses grew from single-digit millions in revenue to tens of millions.
He also worked at Upwork, giving him operating experience across companies that later entered public markets. WageWorks, Cornerstone OnDemand, and Upwork all went public — a useful résumé for an investor studying how software businesses move from early traction to scale.
Jacobsohn became a venture partner at Emergence Capital before joining Norwest in 2014. He is now a partner at Norwest, a venture firm based in Menlo Park, California, where his portfolio spans a wide range of company stages and software categories.
A portfolio built around enterprise software
Jacobsohn has 15 active portfolio companies, ranging from pre-revenue startups to businesses generating more than $300 million in revenue. That spread gives him exposure to the awkward middle of venture investing, where a company must turn an idea into sales and then turn sales into a durable business.
Much of his portfolio sits within finance and HR software, although he also invests in supply chain and construction technology. The mix reflects a focus on systems that handle core business work rather than software built only to decorate a presentation.
His investment conversations cover where the market still has openings for finance software and how far companies should trust AI with accounting work. Those questions put technology beside risk: software may automate parts of accounting, but the decision to hand over financial work remains a business judgment.
That judgment matters because finance software sits close to money, records, and company operations. Jacobsohn’s focus on AI and accounting is not a general exercise in futuristic enthusiasm; it is a test of where automation fits inside work that companies already depend on.
The sales test behind the investment decision
Jacobsohn also examines the competitive space around large HR platforms. His view is that HR startups may be better off attacking the secondary products of large platforms, rather than confronting their strongest products head-on.
That strategy gives founders a specific problem to solve: find a neglected product area where a startup can establish value before challenging the platform’s center of gravity. Large software companies do not need to lose their main product for a startup to find an opening.
The same practical lens shapes Jacobsohn’s CEO test. Before investing, he tests whether the CEO can sell — not only the product, but the company’s reason to exist and the case for customers to change their current systems.
For startups with little or no revenue, that ability can matter even more because the business has fewer operating results to present. For companies generating more than $300 million in revenue, the test does not disappear; the sales challenge changes as the organization grows.
Norwest gives Jacobsohn a large platform for making those decisions. Founded in 1961, the firm manages $15.5 billion and is investing out of its 17th fund, a $3 billion vehicle raised in 2024.
Norwest has backed more than 700 companies across enterprise, consumer, and healthcare sectors. Against that scale, Jacobsohn’s sales test sounds less like a quirky interview tactic and more like a filter shaped by years of watching software companies grow.
The lesson is blunt: enterprise software still needs someone who can win trust, close customers, and explain why the product deserves a place in the workflow. AI can change the accounting process, and a startup can target a secondary HR product, but the CEO still has to sell the bet.
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