Do you want your salespeople to become world-class? Then you should teach them it’s what they do after the customer says “yes” that truly matters. Upselling is a surprisingly easy thing to pull off when approached properly and it’s often the difference between a company that subsists and a company that thrives.
When I work with new salespeople, I find that most are extremely focused on the one-off sale. They get tunnel vision. They’re so focused on getting the customer to initially give in that when it happens, they think they’ve won.
Sure, they’ve earned the company money, put some commission in their pocket, and they are one step closer to their goal, but being an effective salesperson means recognizing that getting a customer to say “yes” is only the beginning.
Upselling is the secret to lucrative sales
This is why upselling should be a major aspect of your team’s sales strategy. With the probability of selling to an existing customer being at the high end of 70%, upselling should be pushed – though tactfully – at every opportunity.
You know what makes upselling truly easy? Three words: Configure, Price, Quote.
CPQ makes upselling a seamless part of the sales process, which makes it a must-have addition to your team’s sales toolbox.
CPQ gives insights into customers’ needs
A successful upsell requires you to know your customer inside and out. More than that, it requires the salesperson to know the customers’ wants, needs, and desires. CPQ makes upselling simple because it makes this customer familiarity automatic and fluid.
CPQ’s guided selling flows are built on a rules engine that your team configures in the backend. These rules define how products fit together, which options are most relevant, and what upgrades make sense based on each customer’s situation.
So when a rep starts building a quote, CPQ already knows what the customer needs. It’s been guiding them through the process the entire time by asking a set of questions, narrowing down choices, and collecting all the critical inputs.
That insight doesn’t just lead to accurate quotes. It opens the door to upselling. Because CPQ understands the full context, it can automatically surface:
- Better bundles
- Relevant upgrades
- Complementary services
The software can even track customers’ previous orders (if applicable) and make purchase recommendations based on that data. This removes the guesswork and makes the salesperson come across as caring and attentive, all of the qualities customers covet in qualified sales reps.
9 strategies to optimize upselling with CPQ
CPQ is your secret weapon for driving bigger deals without pushing irrelevant products. That’s already established. But you need to set it up the right way.
Here’s how to turn your CPQ into a silent upselling machine:
1. Build intelligent bundles.
Don’t just group products together; build bundles that solve real problems. Use your rules engine to combine complementary items that enhance the core offer. Think hardware + service + training. Or software + integration + support. If it saves your buyer time, money, or effort, it sells itself.
2. Set smart upgrade paths.
Define clear paths that help buyers grow into more advanced solutions. Your CPQ should know when a customer qualifies for a higher-tier product and surface it at the right time. Base it on user count, feature gaps, usage data—whatever makes the upgrade feel obvious.
3. Use conditional logic for timing.
Timing is everything. Set rules that trigger upsell prompts only when they make sense. For example, only show a training add-on if the customer is buying multiple licenses. Or prompt a warranty when high-value equipment is selected. Irrelevant suggestions kill trust—precision builds it.
4. Highlight ROI, not just features.
Upsells fail when they feel useless or sales-y. Use your CPQ to show value, not just more stuff. Tie every upgrade to a business outcome: faster onboarding, higher output, lower risk. Add short blurbs or tooltips to explain why the upsell is worth it.
Pro tip: This is easy to do with DealHub CPQ because it centralizes sales enablement content and uses special playbooks to guide selling.
5. Personalize based on customer segment.
Segment-based selling is a game changer. Enterprise buyers don’t need the same upsells as SMBs. Use CPQ logic to tailor upsell flows based on industry, company size, or use case. The more tailored the offer, the less it feels like a sell.
6. Include visual or usage-based comparisons.
Help your reps sell with confidence by giving them visual tools. Comparison tables, “good-better-best” views, or usage-based nudges (e.g., “You’re hitting limits—upgrade now”) can all be built into CPQ flows. It makes the upgrade feel like the next logical step.
7. Auto-suggest complementary services.
Don’t stop at products. Use CPQ to recommend professional services, onboarding packages, priority support, anything that adds post-sale value. These often have the highest margins and help cement long-term relationships.
8. Align upsells with pricing approvals.
Here’s where most teams blow it: they separate upsells from pricing governance.
If your reps need approval to discount the core product but not for approved upsells or add-ons, that’s leverage. Set up your CPQ to make upsells frictionless while keeping heavy discounting under control.
Reps will learn to protect margin by shifting value into upsell items that don’t need special sign-off. And you keep control over pricing without slowing down deals.
9. Analyze historical deal data.
The best way to predict what will work? Look at what’s worked before. Feed your CPQ rules engine with closed-won data. Which upgrades close faster? Which bundles get accepted most? Let past performance train future logic and you’ll keep improving your upsell game.
CPQ makes upselling simple
Imagine your sales force being able to sell add-ons, upgrades, and bundles the moment the customer nods their head in the affirmative. While other sales organizations are focused on single sales to meet the quota, your salespeople will be rising through the ranks and maximize revenue.
With the probability of selling to an existing customer being at the high end of 70%, upselling should be pushed – though tactfully – at every opportunity. Don’t merely leave the process up to your salespeople. Put CPQ in their corner and have the job done right.
