How involved should a startup's executives be in individual sales deals?

Dave Kellogg · Jan 31, 2024

A founder-CEO should be deeply involved in any deal that is material to the quarter — including meeting the customer in person and knowing the people by name — and not doing so is negligence

If the board asks what went wrong on a million-dollar deal in a $5-10M quarter, 'I don't know, ask Joe' is a terrible answer

Scope: scaled to the materiality of the deal to the quarter; especially for companies doing $500K-$1M deals

35:06 20VC: The Metrics That Matter in SaaS Today; Why CaC Payback is Flawed & CAC Ratio is Better, Why You Need to Hire Three Sales Reps at a Time, How to Forecast in 2024 & Biggest Mistakes Made Forecasting & How to Make Customer Success Sell More with Dave K

Patrick Forquer · May 11, 2026

CEO-to-CEO bake-offs are rare in enterprise software generally but normal in Legora's deals, and that scrutiny is reasonable

For a top law firm this is such an important decision that they want to know who they are betting on — vision, values, product strategy and the chops of the delivery team all get gone over with a fine tooth comb

Scope: 'rare in my career' but not at Legora

42:31 20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

Craig Courtemanche · Dec 4, 2023

A CEO should stay out of deal negotiations and commercial terms but talk to customers constantly; there is nothing more important a CEO can do, and you cannot spend too much time with the people you serve

He wants non-transactional, long-term partnership relationships built on joint strategy rather than being the closer

Scope: he has held this line for five or six years; he gets criticised internally for spending too much time on it

32:52 20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

Steve Goldberg · Dec 13, 2023

CEOs should never be the ones closing deals; their role is to give the customer confidence in the company's vision and to align with peer executives.

Closing is the CRO's job; big deals are won because the customer buys into the company, culture and innovation via alignment across CFOs, CTOs, CPOs and CEOs, not because the CEO closed it.

Scope: applies to large seven- and eight-figure deals

26:56 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

Doug Adamic · Sep 8, 2023

Marquee accounts require executive sponsorship, but it need not be the CEO every time — the responsibility should be load-balanced across the executive leadership team

The executive leadership team has a responsibility to represent the organization in go-to-market for larger marquee companies, but no one executive should carry all of it

31:50 Exec sponsorship load balanced across leadership

Mark Goldberger · Apr 19, 2023 · hedged

For any trajectory-changing large deal, not just the CEO but the entire executive team should be involved

45:31 Whole exec team on trajectory changing deals

Chris Degnan · Nov 10, 2023

A sales leader personally running every major deal becomes the bottleneck that slows deals down; scale comes from hiring leaders with the same sense of urgency and handing them the transactions entirely

His own calendar can't be in Europe, Asia and Texas at once, so any deal that needs him waits — whereas a trusted leader runs those transactions and only asks for what he needs

29:52 Leader in every deal becomes the bottleneck

Chris Degnan · Nov 10, 2023

A CRO should join deals of any size, including small first-logo deals, rather than only large ones.

Opening new customers and developing the sales team by leading from the front is the most valuable and enjoyable part of the job.

51:45 Exec joins deals of any size to lead from the front

Amit Bendov · Sep 12, 2025

CEOs are still needed in large deals because the customer is buying the vision of the company and wants direct access to the person who can decide and fix things when they go wrong.

On seven- and eight-figure investments the buyer wants to know they can call the CEO in the middle of the night, and the CEO can also make exceptions outside the ordinary.

49:53 Buyers want direct ceo access on large dollar deals

Amit Bendov · Sep 12, 2025

A CEO should respond to and take calls with customers of any size, but should not be pulled into deals to rescue reps who failed to articulate value.

The rep has to do their own work; the CEO isn't there to save the day with charm.

50:43 Ceo takes any size call but does not rescue failed reps