Masterclass: 3 Proven Strategies for Increasing Deal Size

In a tough market, the key to hitting ambitious revenue targets despite shrinking pipelines is making the most of every opportunity (AKA, increasing your deal size!)

But consistently winning bigger deals requires intentional alignment on strategy across the entire GTM team. In this masterclass, we dove into proven tactics from experienced sales, CS, and RevOps leaders for moving up-market.

Featuring top GTM leaders:

Multi-Threading and Managing Stakeholders

“A good starting point in moving up-market is being extremely honest about where you’re going to win. And then you need to find the people who are actually incentivized to solve this problem.” - Kyle Norton

Bigger deals = bigger buying teams. When selling enterprise deals, multi-threading effectively and managing multiple stakeholders across multiple teams is an essential skill.

Focus on your best-fit customers

When moving up-market, the most successful teams tighten their ICP. Your value props and the problems you solve need to be bigger, broader, and more important when targeting larger customers – so if you’re trying to sell larger deals, focus your efforts on your best-fit buyers where you can truly make an impact and help them achieve their goals.

After the close, you need to deliver on the value you promised these customers (and meet higher expectations), so make sure your team has the resources and support required.

Map out the organization

CFOs and other executives are more important than ever to getting deals done today – sales teams need to build thoughtful strategies about how to reach key decision makers. That’s why for enterprise deals, it’s essential to create org charts to map the buying team’s roles and relationships.

Don’t ignore the “connective tissue” teams, like RevOps, IT, or People Ops, which can play a crucial role in implementing solutions and owning the budget.

Find, nurture, and arm your champions

A champion is someone who has "skin in the game – they’re willing to invest time and effort into the sales process,” says Anne Pao. They open up about the challenges their organization faces and are willing to strategize and discuss deal specifics. 

Anne recommends searching for champions who understand problems that are important to multiple executives or areas of the business. By doing so, you can align your solution with the company’s broader goals and increase your chances of success.

Next, arm your champions with the necessary tools and information to sell your product internally. Champions often face pushback and need to defend their decision to purchase the solution. To support them, build a strong business case WITH your champion and other key stakeholders – aligning on their challenges, goals, how your solution will help, and ROI.

Aligning Sales and Customer Success

"It's not about being salesy; it's about establishing a partnership. When you involve customer success, you're showing buyers how we'll make this work together." - Brad Rosen

Another reason selling larger deals requires different strategies: the expectations of larger customers are higher. They expect vendors to be well-prepared and have robust support systems in place. That’s why bringing your customer success team into the deal early can pay off.

Helping buyers envision the future state

As Anne said during the session: “No buyer cares about the sale. They care about what happens after the sale.” Often, salespeople are afraid to discuss topics beyond the sale itself and focus solely on closing the deal. But buyers are ultimately interested in achieving value and their desired outcomes. By bringing in CS, buyers can more easily envision themselves in the partnership long-term – understanding more details about what will happen after they buy.

Avoiding potential pitfalls

If sales isn’t aligned with CS and product about how they plan to support enterprise customers after the close, expectations might not be met – leading to burned bridges. Involving CS in the sales process facilitates conversations about the implementation process, identifying potential pitfalls and mitigating risks.

Leveraging the Power of RevOps

"We're the connective tissue, the glue that understands how different parts of the business work together.” -Anne Pao

An often overlooked team in GTM, RevOps can have a huge impact on helping organizations move up-market and increase ACV. 

“We are the team that understands the leverage points and the linkage points in the business,” said Anne, describing integrators like RevOps as the "connective tissue" that have a multi-dimensional view of the business and are responsible for supporting and partnering with multiple teams and stakeholders.

RevOps teams have insights into the activities and numbers that drive KPIs, and are also essential in the post-sales phase. It’s often RevOps that handle implementation, training, and contract renewal. Avoiding engagement with these teams is a red flag, Anne says, since they play a crucial role in making the implementation successful.

Aligning sales, CS, and RevOps in the push to move up-market and increase deal size is critical. Although many of the specific strategies and tactics for selling enterprise deals are different than smaller deals, the overall focus is the same – building trust and demonstrating value to the right people at the right companies.

Interested in learning more about how to up-level your enterprise deal execution? Book a demo of Accord to see proven playbooks and strategies from 100+ GTM teams like Figma, Stripe, and Affirm.