Gabe Cabrera

Vice President of People and Projects
@ Summit Strategy

From no proposal experience to closing multi-million dollar deals, here’s how Gabe Cabrera spurred a career of nearly two decades in proposals and rose to the ranks of Vice President.

From Proposal Coordinator to VP

The snowball effect is the perfect metaphor to describe my proposal journey. ❄️

Starting with zero proposal experience—I went on to secure $100M+ wins with 15+ years in the RFP industry—none of which was my intended plan. Yet, I embraced every challenge, every lesson learned, and every opportunity.

The road from Proposal Coordinator to Vice President of People and Projects at Summit Strategy was, at times, difficult, but my calm and diplomatic approach well-equipped me to rise to the challenge.

The $100M Deal That Changed Everything

Early in my career, I started in a recruitment role at a federal contractor startup. And as the startup grew, so did the need to respond to RFPs. Seeing an opportunity, I quickly shifted gears and moved from Recruitment to Proposal Coordinator—despite never managing a proposal.

Even though I was operating with zero proposal experience under my belt, the Senior VP of Sales recognized my ability to navigate RFP responses successfully. And luckily, she offered to teach me everything she knew. I seized the opportunity, jotting down everything and anything that would help me grow.

Snowballing from there, my coordinator role soon morphed into a Proposal Management position, built just for me, where I took on more (and significantly larger) deals.

Using everything I learned from our Senior VP of Sales, I won the startup’s first-ever Prime Federal Government contract—closely followed by another Prime contract win, resulting in over $100 million in revenue.

It was a massive win for the company and a huge professional milestone, proving that I had what it takes to thrive in the fast-paced proposal industry. Despite initially falling into the role, I was suddenly (and surprisingly) passionate about pursuing this rewarding career path.

There’s No “I” in Proposals: Embracing a Player-Coach Mentality ⚽

One of my biggest fumbles starting in my career was not networking sooner.

As a young professional in a totally new field, I was focused on just getting through each day. Thankfully, great mentors encouraged me to get involved in the industry to learn from others and build connections.

My first true boss in the proposal field was all about the player-coach mentality. She helped me understand the balance between actively engaging in the day-to-day tasks while providing guidance, mentorship, & leadership.

Coach: Leads by Example

Her coach mentality stuck with me and proved extremely useful as I entered roles like Team Lead and Director later in my proposal career. To this day, at every opportunity, I encourage and enable my team to improve their skills, grow professionally, and network, network, network.

Player: Operates With the Team

The best coaches are only as good as their players. And the best way to know your players is to live a day in their shoes. I routinely jump back into functional duties while building a collaborative environment where teamwork, communication, and diplomacy are valued.

My Unofficial Title: Resident Diplomat

RFPs can get intense (thank you, extra tight deadlines), which means emotions follow. That’s why I’ve embraced my unofficial title as Resident Diplomat to avoid unnecessary conflict while empowering my team to meet our goals.

My diplomatic approach, which is a skill that can be developed, helps me problem-solve, level-set, and maintain momentum in the fast-paced RFP world.

What’s more, I’ve always had a naturally low resting heart rate. You’d be surprised how DNA wiring can benefit you in the most surprising places. 😅

When the wild and windy RFP weather rolls in, be the eye—not the storm.

Taking Pride in My Path to Proposals

When I started in this field, proposal support was a role that you happened upon. Nearly 20 years later, I’m now the VP of People and Projects with Summit Strategy, a proposal and marketing development firm. I help proposal consultants and clients with strategic planning, proposal development, branding, and training.

From starting as a Proposal Coordinator, making about $60k, to working my way up to very rewarding leadership roles, I’m always proud to advocate for proposal management as a career, not simply a job. I wear my continued growth and evolution in this exciting field as a badge of honor.

Lessons from a Coordinator Turned VP ❤️

If you’re new to proposals, know that this field isn’t “just a job” anymore. Gone are the days of proposals acting as a support function. Proposal professionals are critical strategic players that have a real impact on the bottom line every day and should be viewed with respect. So, how do you climb the ladder and thrive in your proposal career, while staying grounded?

Build Your Foundation

As you move forward, remember that great communication skills (including project management, active listening, and empathy) are table stakes. Prioritize them. And never be afraid to learn something new.

Build Your Network

Don’t make the same mistakes I did. Lean on your network. Seek great mentors who will encourage your development and peers who make up a dependable circle of support.

Build Your Career

While the corporate world can seem to put bullish leadership on a pedestal, I’ve found a calm, grounded approach is much more effective. The way I see it, diplomacy was the key to my advancement from Coordinator to Vice President.

With these lessons in mind, you’ll be well-equipped to keep your heart rate low when pressure is high and skyrocket your career.

The Shortlist

Get the insider newsletter for proposal teams, delivered to your inbox every month.

The Shortlist

Get the insider newsletter for proposal teams, delivered to your inbox every month.