Closing larger SaaS deals is an upmarket transition, not simply a matter of asking for a bigger contract. Jason Lemkin’s advice is to align sales leadership, product readiness, deal scope, customer support, sales-cycle expectations, and account coverage with the price tier you want to reach. His recommendations are practical guidance, not independently tested guarantees.
What changes when you move upmarket?
A larger deal usually asks a buyer to make a broader commitment, and that can bring more scrutiny, product requirements, stakeholders, and time into the sales process. Lemkin’s central point is that a company must build the capabilities to serve the intended deal size, rather than expecting a few unusually large contracts to happen through the same approach it uses for smaller customers.
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He frames the transition as a process: “Going upmarket is a process. It’s well understood.” That does not mean every company needs the same enterprise features or sales model; the right changes depend on the buyers and price tier it is pursuing.
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Six ways to pursue bigger deals
1. Hire a sales leader who has sold at your target price point
Lemkin recommends hiring a CRO or VP of Sales with experience selling at the high-end deal size the company wants to reach. The relevant test is not simply whether a candidate has held a senior sales title, but whether they have closed deals near the intended price tier. In his view, that experience can help the company set pricing closer to the high end customers will accept.
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Make the target concrete in the hiring conversation: ask what deal sizes the candidate personally sold, what buying process those deals involved, and how they would adapt the company’s pricing and sales motion. The advice is to match leadership experience to the ambition; the source does not establish that this hire alone will produce larger contracts.
2. Treat enterprise readiness as a product commitment
An SMB-focused product team may resist work that larger buyers ask for. Lemkin names SOC 2, HIPAA compliance, siloed data, and integrations as examples of potential requirements. They are not universal requirements for every enterprise customer, and the list should not be treated as a checklist to implement without buyer evidence.
Use prospect conversations to identify which requirements actually block a purchase, then assess the cost and product implications of meeting them. Security and compliance commitments can involve ongoing work, while data separation and integrations can affect architecture and maintenance. The decision is whether the opportunity and strategic value justify the investment—not whether “enterprise” automatically means building every feature a prospect requests.
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Lemkin advises sellers to pursue all seats and more revenue upfront, while also recognizing that the customer relationship and company brand may not yet have earned that ask. The tension is between capturing a broader commitment now and matching the request to the buyer’s readiness.
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Make the full-scope option clear, but connect it to the customer’s actual rollout, users, and expected value. If the buyer is not ready to commit to every seat, a smaller starting scope can preserve the relationship and leave room to expand as adoption and trust develop. Lemkin’s advice is to be “aggressive — but learn also to be patient,” not to force an oversized deal that the buyer cannot support.
4. Put people around the customer before and after the sale
Lemkin treats customer-facing help as part of the upmarket motion. He points to forward deployed engineers, presales customer help, and customer success as ways to support engaged, happy customers and organic land-and-expand. In this framing, those functions are not only post-sale overhead: they can help a prospect evaluate the product and help a customer realize value after buying.
He offers “as much as one CSM per $500k in ARR if you can afford it” as a rule of thumb. This is Lemkin’s heuristic, not an independently established staffing benchmark; it should not be read as a universal ratio. Consider the complexity of implementations, level of service promised, customer needs, and the economics of the business before deciding how much coverage to provide.
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Larger deals may take longer than smaller ones, so a young company should not build its plan around every major prospect closing immediately. Lemkin uses the claim that “you can’t close a $1m deal in 30 days” as an illustrative judgment about an unrealistic expectation for a new-ish startup, not as a measured benchmark or rule that applies to every company and sale.
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Patience does not mean accepting avoidable delay. Track where a real opportunity is waiting—such as evaluation, security review, stakeholder alignment, or contracting—and work with the buyer to clarify the next step. The goal is to shorten the process where possible without forecasting a quick close simply because the contract value is attractive.
6. Visit the accounts that matter most
Lemkin recommends in-person contact alongside remote selling, especially for top prospects and customers. He argues that visits can affect deal size, duration, risk, and upsell, but the source does not quantify those effects. Treat travel as a targeted choice: use it where direct contact can help advance an important relationship, rather than assuming every account needs the same level of in-person coverage.
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Before committing to a larger-deal push, make the six choices explicit. This is a way to apply Lemkin’s recommendations, not a tested comparative framework.
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- Target deal size: Define the price tier you are pursuing and whether your sales leader has sold at that level.
- Buyer requirements: Separate verified security, compliance, data, and integration needs from features that are merely presumed to be “enterprise.”
- Opening scope: Decide what a full commitment would include and what smaller, credible starting scope could lead to expansion.
- Customer-facing capacity: Plan presales and customer-success support around the service your buyers and customers need, rather than treating one staffing ratio as a rule.
- Sales-cycle assumptions: Forecast realistic timing for larger opportunities and identify steps that can be made more efficient.
- Account coverage: Decide which prospects and customers merit in-person engagement in addition to remote contact.
Lemkin also cites Salesforce doing “nine figure deals” and Box and Slack doing “many seven figure deals” as examples. The SaaStr page does not provide a year, underlying data, or independent validation for those descriptions, so they are illustrations in his argument rather than benchmarks for what another company should expect.
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