Many B2B SaaS companies serving SMBs feel the siren call to move upmarket, and for good reason: bigger contracts, greater expansion potential, and harder-to-displace customers.
But plenty of companies have crashed on the rocks in pursuit of it, spending years investing in sales, product, and infrastructure, only to find the returns don’t justify the cost.
In this post, I’ll explore the upside and risks of moving upmarket, with practical recommendations on how product marketing can help set your team up for success, based on my experience in the field.
Why companies move upmarket
- Larger contracts with room to expand. Enterprise sales typically involve more users, business units, and use cases, so contract value starts high and can grow over time as a first deployment opens the door to the rest of the organization.
- Stickier revenue. Enterprise deals usually lock in multi-year contracts. Once your product is embedded in workflows and reporting, replacing it becomes a hassle, driving stronger retention and more predictable revenue.
- Credibility that compounds. A recognizable enterprise customer strengthens case studies and references, and makes the next enterprise deal easier to win.
Common challenges when moving upmarket
- A long runway to revenue. Enterprise growth takes time and a significant investment of product and GTM resources. While deals under $25K ACV commonly close in 30 to 60 days, enterprise deals between $100K and $500K often take six to nine months. Security reviews, legal redlines, procurement, and annual budget cycles all add time. Without sufficient resources and milestones that reflect enterprise sales realities, leadership can lose patience and pull the plug before the strategy has a chance to gain traction.
- A credibility gap. Credibility flows downmarket more easily than up. A company known for serving large enterprises often gets a halo effect when it moves into small business, but the reverse is rarely true. Enterprise buyers want evidence that the product can meet their needs at their scale, and success with smaller customers may not be enough to convince them.
Six product marketing decisions that set you up to win
Enterprise buyers have different needs, more complex purchasing processes, and higher expectations for the vendors they trust. Product marketing sits at the center of the shift: which segment to pursue, how to position and price for it, what the product needs to compete, and how sales wins the deal.
1. Choose a segment where you have a credible right to win
Enterprise isn’t one market. A healthcare group and a global retailer have little in common beyond their size. Trying to serve both will spread your team thin across buyers with different needs. Get specific about the industries and personas you want to target.
Start with a win-loss analysis of larger deals. Look for patterns in where you win, where you lose, and which competitors show up. Pay particular attention to frustrations with existing solutions; they can reveal opportunities your platform is well positioned to address.
Then choose a beachhead where you already have customers, references, and a reason to win. If you serve a particular vertical in SMB, moving upmarket within that industry is a natural next step. You already understand the workflows, regulations, and buyer language, and have customers who can vouch for you. Moving upmarket into a new industry means building credibility on two fronts at once.
2. Reposition around the problems that matter at enterprise scale
As companies grow, the people using your product and the jobs they need it to do often change. At a small business, users wear multiple hats and value ease of use and time savings. At an enterprise, users may specialize in that function and tolerate more complexity. They may care more about control, customization, reporting, and cross-department coordination. Your positioning needs to reflect those priorities, with a business case that shows why they matter.
Test the new positioning with buyers in your target segment before it goes into the pitch deck or onto the website. Put two or three value propositions in front of them and listen for the language they repeat, where they push back, and what evidence they need. Messaging that resonates with a single-location owner may fall flat with a VP responsible for hundreds of sites.
3. Close the product gaps that block deals
Product marketing should partner closely with R&D, bringing market and customer insight into product strategy. Moving upmarket makes that partnership even more important because product gaps can become deal blockers.
Use competitive intelligence, win-loss findings, and sales call analysis to identify what keeps you out of enterprise accounts. Depending on your market, buyers may expect role-based permissions, centralized administration, integrations with their systems of record, consolidated reporting, uptime commitments, SSO, audit logs, and evidence of strong security practices.
Work with product and engineering to define the minimum enterprise-ready offer. Separate the requirements that block deals from features that differentiate you and requests that serve only one customer. Validate priorities with three to five design partners in your target segment before committing them to the roadmap.
4. Create enterprise pricing and packaging
The pricing model that works for SMBs may not translate to enterprise. Start with your unit of value: what grows as customers get more value from your product? Depending on the business, that might be users, locations, business units, or data volume. Enterprise buyers may also need capabilities that SMBs rarely require, such as centralized administration and governance across business units or hundreds of locations.
Keep the model simple. Adding complexity just because you’re selling to enterprise creates more friction in procurement and makes it harder for buyers to understand what they’ll pay as they grow. I recommend packaging around the jobs customers need to get done, including the capabilities required to deliver that value, while building in flexibility for different deployment sizes and expansion paths.
Before rolling out new pricing, test the packages and pricing metric with target buyers. Model how discounting, deployment size, and expansion affect deal economics.
5. Partner with Marketing on an enterprise GTM motion
Enterprise demand generation relies less on high-volume acquisition and more on reaching the right accounts and engaging the buying committee. Product marketing should work with demand gen and field marketing to prioritize channels and programs for your target segment. Build account-based campaigns around your beachhead list, create content for the different buying roles, and develop an analyst relations plan if analysts influence purchasing in your category.
Your website and sales assets also need to speak to enterprise buyers. Add dedicated enterprise pages or consider separate sites if the audiences and propositions are substantially different.
6. Enable the field to close enterprise deals
Enterprise selling requires different skills and a different sales motion from high-volume SMB sales. Start with one or two experienced enterprise sellers who can test the approach before you scale the team, with an eye for people who can navigate complex buying committees, think creatively, and operate without a fully established playbook.
Treat your first enterprise deals as a learning lab. I’ve joined early sales calls and delivered the pitch myself to see how the positioning holds up with real buyers. Capture what you learn, including qualification criteria, effective discovery questions, and common objections, to build an enterprise sales motion grounded in what works in the field.
Build enterprise-specific demo environments and pitch decks, and make sure pipeline and revenue forecasts account for longer sales cycles, more stakeholders, and additional procurement steps.
Map the buying committee during discovery and equip sales with the materials each stakeholder needs:
- Security and IT: A trust center, a completed standard security questionnaire, and your SOC 2 report.
- Finance: An ROI model grounded in customer data.
- The executive sponsor: Case studies from customers operating at a comparable scale.
- The functional leader and end users: An implementation plan with clear owners and success criteria.
- Procurement and your champion: A mutual action plan with dates, owners, and a clear path to signature.
Questions to answer before you commit
Use these to score the opportunity with the right-to-win framework.
Right to win
- Why would our target buyer choose us over the incumbent or a purpose-built enterprise vendor?
- Does our credibility carry into this segment, or do we need new references and proof?
- Are we winning on differentiation, or on customization and price?
Economics and commitment
- What contract value, sales cycle, acquisition cost, and margin should we expect?
- How much will we invest before enterprise revenue becomes material, and how long are we prepared to fund it?
- What evidence would cause us to change course?
Make the move with evidence
Companies that move upmarket well can name a specific enterprise segment, describe the problem they solve in that segment’s own terms, point to customers who prove it, and show economics that hold up over the life of the account. They get there by gathering customer and market evidence before the big sales hires and roadmap commitments, not after.