Moving upmarket isn’t just a nice-to-have for most SaaS companies – it’s often the difference between building a sustainable $100M+ ARR business and getting stuck in the mid-market quicksand.
Julie Iskow, CEO of $600m+ public SaaS leader Workiva joined Norwest Venture Partners Sean Jacobson at SaaStr Annual for a deep dive on going More Enterprise.
Just look at the numbers: Enterprise customers bring 95%+ best-in-class retention vs. 85% in mid-market. That compounds dramatically over time. And while most SaaS companies (80% according to Marc Benioff) start downmarket, the ones that successfully make the enterprise transition are the ones that build lasting value.
Here are the 5 key lessons from Workiva CEO Julie Iskow on how to make that transition successfully:
1. Start Planning for Enterprise Earlier Than You Think
The biggest mistake SaaS companies make? Waiting too long to start their enterprise planning. Even if you’re still focused on SMB and mid-market today, you need to be laying the groundwork for enterprise now:
- Make your enterprise aspirations visible to everyone in the company
- Build your product with enterprise-grade configurability and integrations from day one
- Start hiring people who have enterprise DNA and relationships
- Choose tools and infrastructure that can scale with you
As Julie puts it: “The decisions you make today will either make your enterprise transition easier or force you to rebuild everything later.”
2. Land One Strategic Enterprise Logo Early
You don’t need to wait until you have every enterprise feature to land your first major logo. Look for an innovative enterprise customer who:
- Is willing to be a development partner
- Has clear needs you can solve today
- Will give you access to testing environments
- Can help shape your roadmap
The goal isn’t to build custom features – it’s to deeply understand enterprise requirements and bake them into your core product. One great enterprise reference customer is worth 20 mid-market logos.
3. Build the Right Team for Enterprise Success
Enterprise selling requires a fundamentally different skillset. You need:
- Sales leaders who understand complex, multi-stakeholder deals
- Customer success teams ready for high-touch support
- Legal expertise for enterprise contract negotiation
- Product leaders who can balance current needs with future vision
Pro tip: Hire enterprise reps in pairs. If both succeed, you’re ready to scale. If one does and one doesn’t, you know it’s the person not the motion.
4. Master Enterprise-Grade Operations
The operational bar is much higher in enterprise. Focus on:
- Building robust security and compliance (SOC 2, ISO 27001)
- Automating customer onboarding/offboarding
- Creating enterprise-grade support processes
- Developing procurement relationship expertise
- Having clear data handling procedures
5. Think Platform, Not Point Solution
Most successful enterprise companies win with platforms, not single products. As you move upmarket:
- Build sharable services across your platform
- Plan for multi-product expansion
- Focus on configurability over customization
- Create integration frameworks
- Enable workflow automation
The results can be dramatic – Workiva now counts 88% of the Fortune 100 and 85% of the Fortune 500 as customers. While enterprise deals may start small ($25-50k ACV), they often grow to $1M+ as you expand across the organization.
6. Build a Strong Customer Advisory Board
Your enterprise customers should be your best advocates and product advisors:
- Conduct regular ROI studies with every major customer
- Create a formal Customer Advisory Board
- Use customer insights to influence product roadmap
- Turn successful customers into public references
- Host executive-level customer events
A strong CAB isn’t just about feedback – it’s about creating a community of enterprise champions who will help you win more deals.
7. Master the Multi-Stakeholder Sale
Enterprise deals aren’t won in a single meeting. You need to:
- Engage with procurement early – don’t treat them as a rubber stamp
- Build relationships with 20+ key accounts in year one
- Get executive sponsorship on both sides
- Never negotiate price with the business buyer
- Document clear ROI and business cases
Remember: The actual buyer is often not the end user. Map out all stakeholders and their motivations early.
8. Focus on Land-and-Expand Economics
Don’t obsess over initial deal size. Many successful enterprise relationships start small:
- A $25k departmental deal can grow to $1M+ enterprise-wide
- Focus on logos over initial ACVs
- Build expansion metrics into your sales comp plans
- Create clear expansion playbooks
- Measure and optimize time-to-expansion
The results can be dramatic – Workiva now counts 88% of the Fortune 100 and 85% of the Fortune 500 as customers. While enterprise deals may start small ($25-50k ACV), they often grow to $1M+ as you expand across the organization.
The Bottom Line
Moving upmarket successfully requires intentional planning, the right team, and relentless execution. But the rewards – higher retention, bigger deals, and ultimately a much larger TAM – make it worth the investment.
Start laying the groundwork today, even if enterprise isn’t your immediate focus. Your future self will thank you.
Remember: The path to $100M+ ARR almost always runs through the enterprise. The only question is whether you’ll be ready when the opportunity comes.
And a related post on Workiva here:
