digest
Short Summary
Main recommendation: Use upselling to increase customer retention by offering account reviews, running Quarterly Business Reviews (which Dan calls EBRs), and training support teams to spot and offer add-ons or upgrades while solving problems. Dan frames this as building expansion revenue, meaning extra money from existing customers to offset cancellations and downgrades.
Key Points
- Expansion revenue is the extra money added from existing customers through upgrades, add-ons, or expanded plans, used to offset contraction and downgrades.
- An account review is a proactive, no-cost check-in where you ask whether the customer needs anything and preview upcoming roadmap items, which creates openings to offer upsells or pre-sell future releases.
- EBRs (Quarterly Business Reviews, though not always quarterly) are scheduled strategic meetings to review goals, projects, and challenges, and they are best suited to customers paying around 10K annual contract value or higher.
- Support selling uses support agents, who already talk to many customers daily, to flag accounts that lack relevant modules and offer them solutions after resolving the customer's problem.
- Dan's coaching client Ryan increased expansion revenue by 10% annually, primarily through the support selling strategy Dan taught him.
Details Worth Noting
- Concrete instructions:
- Offer an account review: email customers proactively, offering a free review to check they are getting value and ask for questions, then present the roadmap and any relevant upsells or pre-sales.
- Set up EBRs at onboarding: set the expectation up front, schedule two to three meetings per year or quarterly, and have the customer commit to a cadence and attendees in advance.
- In each EBR, review the customer's goals, projects, and challenges; loop in other team members to solve challenges; push adoption into more departments; reactivate dormant accounts; and show usage data.
- Use EBR meetings to identify gaps where an add-on, upgrade, or new solution fits, then make the offer.
- Build a support dashboard by adding account tags (plan, revenue level, support level, modules in use) in your support software.
- Run queries to flag accounts not using a given module or meeting specific conditions, then build a targeted list.
- Train support staff to resolve the problem first, then say something like "I noticed in your account this... did you want to learn how you can get this benefit?"
- Have support reach out proactively by phone or email to offer the relevant upgrade or enhancement.
- Dan's example of GoDaddy: a representative proactively flagged an expiring subscription, asked whether the customer still needed it, noticed 27 domains, and suggested a package that would save 10% if domains were renewed the following year.
- Dan notes that account executive versus customer success ownership of expansion is a separate debate he does not cover.
Bottom Line
Upselling works best when it is built into existing customer touchpoints such as account reviews, scheduled EBRs, and support conversations, where you help the customer get more value and offer relevant upgrades at the moment they are most likely to see the benefit.
