Comm-Works | Lead Generation

Designing Prospecting Plays That Opened 20+ New Opportunities

Challenge

Our Inside Sales team at Comm-Works was struggling to break into large enterprise accounts. We needed a more creative, high-touch approach to build trust and generate qualified opportunities in a crowded, competitive space.

Approach

I designed a set of custom prospecting “plays” that layered multiple, carefully orchestrated touchpoints:

  • Email nurture sequences personalized to the prospect’s industry and pain points (pretty standard, but a must have)

  • LinkedIn “Swarming” tactics to build familiarity across the organization, often leveraging 2nd-degree connections for warm intros (more about that in this success story)

  • Curated SWAG packages sent directly to prospects, creating a physical reminder of our brand (this tactic alone booked 5 meetings and led to about 10 qualified opportunities).

  • Such as digital gift cards as thank-you for meaningful engagement and feedback on our services—not a default move, but one that added a thoughtful touch when appropriate.

Every touchpoint was designed to feel personal, surprising, and intentional—interrupting the standard sales noise with something more human and memorable. We weren’t begging for time like other reps —we made prospects feel like we understood their world and had something valuable to offer, which is why we were professionally persistent.

At the same time, I targeted only 3–5 high-value accounts at a time. I mapped out org charts, contacted adjacent employees to gather intel, and slowly worked my way up to true decision-makers—often arriving with warm context and established credibility.

Result

It also gave our team a playbook to use across the organization. This success is what earned me my promotion into my Sales Enablement and Operations Role, where I was able to formalize these tactics and coach others on how to execute them.

The bigger picture? These efforts introduced meaningful, human conversations with enterprise buyers into our outreach standards. Many of new clients actually thanked me for my persistence in getting through to them.

This approach led to over $16M in qualified pipeline across 20 opportunities.

Reflection

Effective prospecting isn’t about shouting louder or carpet-bombing inboxes. It’s about being intentional, relevant, and persistent in the right ways. When outreach shows real thought and effort, it earns attention—and respect.

This experience gave me the confidence to trust my instincts in future roles. In fact, it helped me source and close a $1M deal at Demand Chain entirely from cold outreach—proof that with the right strategy and mindset, even the coldest lead can become your best customer.