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Power Bite: How to Win Larger Deals

Aug 21, 2023 | 3m


How to Win Larger Deals

In my career, I've worked on $10 million+ TCV deals with our partners, and these have been some of the most exciting moments in my sales journey. Yet these deals don’t happen overnight – you certainly don’t go from a $10,000 contract to a $10 million contract right away. To win large deals, you’ll need a longer term, multi-pronged approach, and that takes time. You have to look at where your product is today, how it’s valued in the market, and figure out how to incrementally increase the ACV of your opportunities. 

There are a few ways in which this can be done:

  • Moving Upmarket to Larger Customers

  • Consolidation Plays 

Think about how you can use your solution to displace other point solutions. How can you leverage your product as a foundation with add ons that provide more value as a platform? 

  • Competitive Displacement 

Know the competition inside out. Who are the players in your market? What are their strengths and weaknesses? Once you have this information, communicate and coordinate with your product teams to figure out how to win deals against those competitors. 

There’s a big misconception that large deals are won by the salesperson who delivers a flashy presentation or an impressive deck. I believe that it’s strategy and relationships that will win you larger deals. 

In terms of strategy, there’s an incredibly unique opportunity right now as we’re in a macroeconomic shift, where there is an emphasis on efficiency. A lot of organizations are feeling headwinds, and it’s hard to sell to organizations as they’re cutting sales and marketing spend, or the spend on software solutions. With consolidation plays, you have the opportunity to turn headwinds into tailwinds. If you can spot ways to displace another product and deliver equivalent value for their teams at lower price points, you’re going to get that conversation nine times out of ten. As such, consolidation plays have been incredibly effective in winning larger deals.  

As for relationships, remember – this takes time. To return to the $10 million+ TCV deal I referenced, it was a result of years of ongoing effort and growth. We started off as a point solution for product teams, and eventually added more features that could be used by marketing teams. Eventually, we got all the way up to the CMO level, and over the years of our partnership, we delivered incredible value to the organization and built great relationships with stakeholders along the way too. 

If I think about some of my larger opportunities with buyers, there’s always a personal relationship of growth involved. That is, the product we were selling was helping the buyer get their job done and get promoted within their organization. As a result of the success they’d experienced through our product, we were able to have transparent conversations around pricing and moving upmarket. So that’s my advice to you: think about how you can help your buyers win, as this will help you in the long run. Certainly, beyond just closing big revenue for your company the most rewarding part of these deals is being able to help your customer, see them succeed, and really flourish as a result of your partnership. 

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Mike Donohue

Senior VP, Global Sales | Former Head of Global Sales & GTM, Shopping

Gupshup | PayPal



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