Sealing the Deal with AI: Smarter Contracts = Faster Revenue

Manual quoting systems. Spreadsheet pricing calculators. Approvals in Slack. If this sounds like your sales process, you’re not alone - and you might be leaving revenue on the table. In this session, RevOps Co-op founder Matthew Volm sits down with CPQ veterans Eran Gross, VP of Customer Success at DealHub, and Ryan McDermott, CTO at Thriviti, to talk about how AI-powered quoting tools can help companies streamline their sales cycles and drive faster revenue.

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Why Legacy CPQ Systems Are Holding You Back

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According to Eran and Ryan, most companies they work with are stuck in outdated quoting processes. Sellers waste time jumping between systems, quotes are inaccurate or inconsistent, approvals are scattered, and legal has no visibility until it’s too late. This doesn’t just create internal inefficiency - it negatively impacts the buyer experience too.

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“We know how easy it could be. When we see approvals happening in Slack or quotes living in spreadsheets, it’s painful—because we’ve seen what’s possible.” – Ryan McDermott, CTO at Thriviti

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For a deeper look into how siloed tools slow down GTM teams, check out DealHub’s article on Sales Ops’ Role in a Frictionless Quote-to-Revenue Process, which explores how Sales Operations can orchestrate a seamless Q2R process, boosting revenue and customer satisfaction.

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What Modern CPQ Looks Like (and Why It Matters)

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Modern CPQ systems aren’t just quoting tools - they’re strategic revenue accelerators. With the right platform, teams can build guided selling experiences, automate pricing, enforce discount guardrails, streamline approvals and even empower legal and finance to be proactive partners in the sales process.

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Ryan shared how his team migrated from Salesforce CPQ to DealHub and rebuilt their entire quoting process from scratch after spinning out a business from CenturyLink. The result? A quoting system that legal, finance and sales all love.

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“Usually, you make one group happy. But when our legal team got their hands on the new process and said ‘this changes everything’—we knew we’d built something great.” – Ryan McDermott

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If you're considering this kind of transformation, DealHub outlines how to navigate CPQ evaluations in How to Select the Right CPQ for Your Business, including feature considerations, deployment tips and cost analysis.

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Start Small, Scale Smart

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If your current quoting process is messy, don’t worry—there’s a path forward. Eran and Ryan emphasized the value of starting small and building momentum.

• Launch your CPQ rollout with a small group of users and limited product catalog
• Put up guardrails at first, then refine them as real-world feedback comes in
• Identify internal champions who can advocate for adoption and help troubleshoot
• Treat implementation as a change management project, not just a tech project

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“Give the tool to one seller. When that rep starts getting quotes out in 30 minutes while everyone else takes a week, others will start asking for access.” – Ryan McDermott

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Need more proof that small wins can scale? Don’t miss DealHub’s breakdown of 5 Ways CPQ Amplifies Sales Team Results, where they show how guided selling features aid sales reps by recommending additional products or services that align well with what the customer is already considering.

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The Power of Guided Selling and Role-Based Access

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One standout feature of DealHub’s CPQ platform is the guided selling engine. It functions like a decision tree that helps reps (especially new ones) navigate product and pricing configurations without needing tribal knowledge.

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Admins can also assign role-based permissions, which lets managers or ops override certain restrictions - without opening the floodgates for the whole team. This balance between guardrails and flexibility is key.

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“I had a customer tell me, ‘I could hire you tomorrow and you’d be able to sell my product just using DealHub.’ That’s the power of guided selling.” – Eran Gross, VP of Customer Success at DealHub

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For more insights on guided selling, check out DealHub’s article The Art of Guided Selling, which discusses how guided selling helps sales teams direct customers through the buying process and improve sales process efficiency.

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Thinking About Migration? Here’s What You Should Know

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Migrating to a modern CPQ like DealHub doesn’t have to be a massive, scary undertaking. Ryan shared how to simplify the process:

• Start quoting net-new deals in DealHub (don’t wait for a full migration)
• Align early on your business goals, data cleanup, and approval workflows
• Focus on your future state—not replicating every legacy field and process
• Don’t overdesign for every edge case; build for the 90%

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“Every time you delay implementation by a year, you're just delaying the payoff. Start quoting now - your future self will thank you.” – Ryan McDermott

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For more best practices and technical tips, check out DealHub’s detailed guide on How to Select the Right CPQ for Your Business, which covers timelines, data modeling, and post-go-live considerations.

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If your current quoting process is filled with friction, it’s time to rethink your approach. Modern CPQ platforms like DealHub make it easier than ever to streamline sales workflows, accelerate deal velocity, and empower your entire GTM team - from sellers to legal. Whether you’re starting from scratch or migrating from legacy tools, the right system can turn your quote-to-revenue process into a competitive advantage. And with AI and guided selling in your corner, sealing the deal just got a whole lot smarter.

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👉 Looking for more great content? Check out the DealHub resource center and the RevOps Co-op blog and join the RevOps Co-op community.

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