• Jamie Weinstein McGuinness

Leap Into Sales

250 days ago we launched our business PondLeap! James, Christina & I (Jamie) decided that although we had an idea, the most important thing was to build our business based on our values. We worked together to come up with the values that would shape all of our decisions moving forward. The first value we decided on was “Humans before Business”. We are proud to say that even as a startup where profits keep you going, we have been able to operate with this at the forefront and choose to only work with clients when it is a win/win/win (freelancer/client/PondLeap). We have so much to be proud of, thankful for, and so much excitement about what’s to come!

Where we started: In our first 250 Days PondLeap has:

  • Built a network of 50+ freelancers with areas of expertise from Junior Sales Reps all the way to experienced Sales Leaders covering the full sales cycle

  • Worked with numerous clients on everything from lead generation, new business development, sales management, sales operations, strategy buildout (and everything in between)

  • Have had 20 freelance “Leapers” prospecting and doing lead generation for PondLeap (we are so appreciative of all of them)

  • Hired one of our Leapers Mike Gyetvay to head up our sales as our first W2 employee!

  • Put together a brilliant Board of Advisors (Scott, Medha, Haley, Alex)

  • Joined the WorkBox accelerator (John Wallace, Kelly Pease, Caitlin McAllister, Stephanie Dybel, Tawny Safieddine)

  • Place 10 Leapers on client engagements

  • Had 8 Leap Days and contributed to 10 different Non-Profits

  • Held 16 “Leaper Sync’s” with our Leapers and Freelancers

  • James completed 16 recorded trainings for our network - One of our freelancers Sid did one as well!

  • Built out a Slack community where our network share ideas and learnings

  • Ran 22 LIVE interactive training sessions with our Leapers

  • Altered our offerings and pricing model about a dozen times

  • Created strategic partnerships with 6 different companies

  • Made some amazing swag and a lot of memories

  • Decided to reposition/rebrand ourselves!

For the last 250 days, we operated with the tagline “jump on in”. When we came up with it 8 months ago, the idea was to stop dipping your toe and wading in the water (and a bunch of other cheeky pond-based analogies) when it comes to revenue generation and just “jump on in” (with the help of PondLeap, of course). While that concept still resonates with our clients and freelancers, we have come to realize that what we are doing is a whole lot clearer. The core differentiator we provide to our clients is the teamwork element in helping them take the “Leap Into Sales”.

Where we are going: Leap Into Sales


We have learned (from personal experience as well as what we are hearing from our clients) that developing a plan of attack to start generating revenue for a startup is multi-faceted. There are a lot of chicken and egg scenarios to consider. The most “involved” aspect is the sales team itself (whatever that may look like). Founders know that they need sales and are usually at a loss as to where to begin this process. What comes first - the people or the processes? Do we need to have a large marketing budget or social media following? Is it best to have one full-cycle rep or a lead generation rep and an account executive? Who will manage these reps and hold them accountable to their activities and outcomes? What are the procedures, tools and people that will take this incredibly important aspect of my business off my plate so I can focus on the other 70 hats I’m wearing?

After 250 days, we can confidently say that we help startups, early-stage & international companies leap into sales by developing a targeted strategy, placing & managing the talent & tools, and creating a maintainable solution.

Over the next 250 days, we will be fine-tuning our offerings and partnerships to fit the needs of our clients and prospects. We will be launching a more official “Leap Into Sales” program. It’s an internal program giving people the opportunity to start their sales careers - regardless of their background and experience. (more on this later). And, we are excited to focus on the opportunities we currently have to work with International startups looking to make the leap over the pond.

As Mike stated so beautifully in his LinkedIn post yesterday “the real beauty of PondLeap lies in the opportunities that it provides PEOPLE. Our internal network is composed of individuals from all sorts of backgrounds that may not have had an easy, clear-cut path into the world of sales. There are new mothers looking to return to the workforce after taking time off to spend with their child, there are college graduates that are looking for that much needed experience that every resume seems to require these days (ex: SDR entry level beginner role - 1 year of Sales experience needed... ha), experienced sales vets and gurus that are looking for change or a new opportunity, and I, myself, was a career changer that would've likely had to start over had I not made the right connections.” Our biggest excitement comes with our amazing network. We love helping people who wouldn’t otherwise have an available opportunity Leap Into Sales!

We can’t wait to continue sharing our story and milestones; but, in the meantime, thank you for all your support.






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