Dear SaaStr: What Are Some Tips For Shortening Enterprise Sales Cycles?
First, get a bit zen about it. You can shorten them, often by 20%-30%. And increase the odds they close. But you can’t do the impossible. You can’t change budgeting cycles, the need to do pilots, etc. A bit more on that here:
But there are plenty of things that help:
-
Hire a VP of Sales with Enterprise Experience: A great VP of Sales who’s closed deals at your price point can shave months off your sales cycle. They know how to navigate pilots, engage stakeholders early, and avoid late-stage objections. If your sales cycle is 9 months, they can often bring it down to 6 or 7 months.
-
Get Good at Pilots: Don’t avoid pilots because they sometimes don’t close. Instead, get better at them. Build a team to own pilots and deployments, and ensure you’re setting clear success criteria upfront. A well-run pilot can accelerate trust and decision-making.
-
Ask About Timing and Budget Early: Don’t waste time chasing deals that aren’t ready to close. Ask upfront if the project is budgeted and what the timeline looks like. This helps you prioritize deals that are actually ready to move forward.
- Understand All The Stakeholders Early. And Sell Them, Too. Way too many founders and sellers just sell to whomever inbounded. In the enterprise, there are often 3-5+ other stakeholders. If you also sell to them, the deal progresses faster.
-
Bring in the CEO: Prospects love talking to the CEO. As a founder, you can often help close deals faster by getting involved in key conversations. Set a quota for how many deals your sales team can bring you into without hesitation.
-
Specialize Your Sales Team: Don’t wait too long to specialize. Put bigger deals in the hands of experienced reps who know how to manage long cycles, and let your quick closers handle smaller, high-volume deals. This ensures each deal gets the right level of attention.
-
Embrace Compliance Early: If you’re selling to the enterprise, get ahead on things like SOC 2 compliance and security audits. Being proactive here can remove roadblocks that often delay deals.
-
Run Paid Pilots or Smaller Deployments: Offering opt-outs after 60-90 days or starting with smaller deployments can help prospects commit faster. Prove your value incrementally and build trust along the way.
-
Show Up in Person. This almost always speeds deals along.
Enterprise sales cycles will always be longer than SMB deals—it’s just the nature of the beast. But with these strategies, you can make them as short as practical.
