Selling to enterprise is no easy feat, and it can be a lengthy, complex process. So how do you simplify and speed up your sales cycles?

Michael Sindicich, GM of TripActions Liquid, understands what it takes to close big deals and boost enterprise win rates. He started as the first sales hire at TripActions when the company was small and he helped scale the business to 5,000 customers, 1,200 employees and a $5 billion private valuation. He was the VP of Enterprise Sales until recently moving to help build TripActions Liquid, the company’s new Fintech product offering.

Read on for Michael’s insightful advice for driving faster sales cycles.

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1.   Create a Sales Engine

You need to be strategic about the architecture of your sales cycle, and for that, you should create a powerful sales engine. Here’s how:

  • Align Compensation: If you plan to close enterprise deals, you must be prepared to pay for the right salespeople. As Sindicich says, “One thing that we’ve learned is enterprise sales reps are expensive and worth every dollar that you pay for them …They expect to have aggressive comp plans with really high accelerators.” At TripActions, the sales reps are compensated based on the customer’s adoption and successful use of the platform. This strategy reduces time to revenue since the rep is focused on getting the account up and running.
  • Pipeline Generation (PG): Traditionally, SDRs and marketing teams find the leads and sales reps close the sale. This works for smaller deals, but Sindicich recommends having the sales team build their own pipelines for enterprise-level sales. “Pipeline generation really serves as the fuel for the engine for the sales rep, especially when it gets to the enterprise. Our reps have gotten really good and methodical at PG –– building their own pipeline along with being supported by the SDRs.”
  • Sales Enablement. In its early life, the TripActions team assumed they could scale by hiring more sales reps and replicating their process. Sindicich stresses that this approach will not yield surefire wins. Instead, he suggests building a sales enablement team with onboarding, playbooks, boot camps, and continuing education, especially as the product evolves.

2.   Stop Selling Like a Startup

In your company’s early days, survival might demand aggressive sales motion. However, as you grow, you must be mindful of how to appeal to enterprise and leave the days of hustle and grind behind you.

Enterprise clients expect a high level of security, compliance, and legal protections as a given, so you should have things in place, like GDPR and certifications like SOC-2, PCI, etc. If you don’t have the proper security and legal benchmarks in place, you can drastically slow down your sales process. So it’s worth the effort to invest in bolstering your credibility for enterprise customers.

Additionally, in the beginning, your CEO might be heavily involved in your sales, but as time goes on, this is no longer necessary. Says Sindicich, “When you’re a startup or trying to go upmarket, you oftentimes involve the founders or the CEO, and that can totally slow your deal down. You need to make sure that you’re building a sales team that’s credible and leadership there that can get deals done without involving the founder in every single deal process.”

3.   Pick Your Lane

You need to fully understand your company and product to determine your selling strategy, and you might have to pivot from your original strategy if you don’t see the results you’re after.

For example, TripActions started with a land-and-expand sales strategy, but they quickly learned they had the most success selling top-down: “I think it’s really important to understand the best way to sell your product, and it can vary from commercial to mid-market to enterprise segments, but it’s important to understand that. Then align the entire company, including marketing, behind that.”

4.   Go Higher

Whether your selling strategy is top-down or land-and-expand, try to get someone in a high-level management position involved in the process. Impress the exec with a comprehensive suite of product offerings for a higher chance of closing the deal. TripActions noticed a 40% faster sales cycle when selling to a C-suite or VP rather than initiated with an end-user only. Once they expanded their product offerings, they also noticed a change: The sales cycle dropped from 40 days to 28 days when they were selling a more comprehensive product offering.

5.   Leverage Executives

While you should avoid sales bottlenecks by involving executives in every deal, there are certain situations where your leadership can help your sales teams close faster. For example, the TripActions sales team will sometimes ask their C-suite and board members about any possible networking or connections they might have with a potential enterprise lead. If so, that connection can clinch the sale. Sindicich believes this is an advantage when used appropriately: “We’ve seen a 30% increase in win rate when we’re connected through the board or through the C-level to C-level.”



Key Takeaways

  • Invest heavily in your top-performing reps and create comp plans that align with their success.
  • If you want to scale, you need to start selling in an enterprise-friendly way and leave your startup selling habits behind.
  • Leverage your C-level executives’ connections with potential leads –– that relationship can be instrumental in closing the sale.

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