How to Successfully Upsell Or Cross-Sell Services to Clients
ClientRelations.io
How to Successfully Upsell Or Cross-Sell Services to Clients
Upselling and cross-selling services can significantly boost your business, but mastering these techniques requires strategic insight. This article delves into proven strategies for expanding client relationships, drawing from the expertise of industry professionals. From partnering for growth to solving deeper problems, discover how to effectively increase your service offerings and client value.
- Partnering for Growth Through Strategic Conversations
- Extend Event Impact with Follow-Up Series
- Preventative Maintenance Proposal Boosts Business
- Solving Deeper Problems Leads to Expanded Engagement
Partnering for Growth Through Strategic Conversations
At Redfish Technology, we believe partnering in growth is the right strategy. Selling (or upselling) services implies a one-size-fits-all approach; we prefer building a tailored plan for each company we work with.
One instance that really highlights this approach involved a long-time client in the clean tech sector. We'd built a strong relationship by consistently placing top-tier engineers for them, but during a routine check-in, I noticed something bigger: they weren't just filling roles—they were scaling fast.
Rather than pitch them a new service, I asked broader questions about how that growth was impacting other areas of the business. That opened the door to a candid conversation about the pain points they were feeling beyond engineering—particularly in product management and technical sales. They hadn't considered involving us there, not because they didn't see the value, but because they hadn't connected those dots yet.
So instead of making a hard sell, I framed it as a conversation. I shared some insights from similar clients navigating the same stage of scale and proposed we pilot just one search outside their usual scope. That single engagement not only delivered results but led to an expanded, cross-functional partnership that aligned with their long-term goals.
The outcome was more than additional business; it was a deeper, more strategic relationship. To me, that's the real goal. Recruiting isn't just about filling positions. It's about building partnerships that support a company's full trajectory. When you approach the work through that lens, upselling becomes a natural extension of shared success—not a transaction.
Extend Event Impact with Follow-Up Series
One of our most effective upsells at Gotham Artists came from a post-event debrief — not a pitch.
A client had just wrapped up a successful leadership offsite with one of our speakers and was raving about the energy it brought to their team. Instead of pushing anything, I asked a simple question:
"What are you doing to keep that momentum going over the next quarter?"
That opened the door. They admitted they hadn't thought about continuity, so we suggested a follow-up virtual series with the same speaker — short monthly check-ins tied to the themes from the live event. It was positioned as extending the ROI, not "booking more." And because the speaker was already familiar with their context, it felt easy and natural.
The result? A 40% increase in contract value from that one client — and they've since replicated the model for other departments.
Preventative Maintenance Proposal Boosts Business
After completing a standard roof repair for a commercial client with multiple properties, I noticed their maintenance schedule wasn't addressing preventative care, only reactive fixes. Rather than immediately pitching our comprehensive maintenance program, I asked permission to conduct a complimentary inspection of their other properties and prepared a visual report showing potential failure points with estimated timelines and replacement costs. During our follow-up, I framed the conversation around long-term budget planning rather than immediate sales, showing how our quarterly maintenance program would extend roof life by 7-10 years while reducing emergency repair costs by approximately 40%. This consultative approach resulted in not only a maintenance contract for all six properties but also led to them referring us to their entire business network, ultimately growing our commercial division by 35% that year.
Solving Deeper Problems Leads to Expanded Engagement
Absolutely—upselling and cross-selling aren't about pushing more services; they're about solving deeper problems. One example that stands out was with a long-term client in the e-commerce space. We initially helped them optimize their Shopify store and handle technical SEO. After a few months, their traffic improved, but conversions plateaued. Instead of just reporting metrics, we initiated a conversation focused on business goals—not just rankings.
During our review call, I asked them one simple question: "What's the biggest obstacle between your traffic and actual revenue right now?" That opened the door to a deeper discussion about customer experience. I noticed gaps in their email marketing strategy and user journey flow—abandoned cart emails weren't personalized, and product recommendations were generic.
Rather than present it as an "upsell," I framed it as a natural next step in achieving the outcome they already wanted: more conversions. I showed a small case study from another client who saw a 20% lift in repeat purchases after we implemented segmented flows and tailored content. That made the value clear and concrete.
We proposed a lightweight pilot to start with lifecycle email automation, paired with dynamic content testing. The client agreed, and within 45 days they saw measurable results—not only in conversion rate but also in customer lifetime value. That initial add-on service expanded into a full retention strategy project and increased our engagement with them significantly.
The key was to make the conversation about them, not us. I wasn't selling a service; I was offering a solution to a problem they were already trying to solve. And I believe that's what makes a cross-sell stick—not just when it's relevant, but when it's rooted in listening and aligning with their evolving goals.
