Designing Prospecting Plays That Opened 20+ New Opportunities

Challenge

Our Inside Sales team at Comm-Works was struggling to break into large enterprise accounts—especially IT stakeholders at Fortune 500 companies who tune out traditional outreach. 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).

• Digital gift cards as thank-you for meaningful engagement—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

This approach generated over 20 qualified opportunities and gave our team a scalable playbook to use across accounts. It also earned me a promotion into a Sales Enablement & Operations role, where I was able to formalize these tactics and coach others on how to execute them.

The bigger picture? These efforts contributed to a $16M qualified pipeline and led to meaningful, human conversations with enterprise buyers—many of whom actually thanked me for my persistence in getting through to them.

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 your 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.