Get to know CareerDash: Paving the way for upward mobility in client facing careers through their high-touch and high-outcome programs.

LearnLaunch Fund + Accelerator
4 min readSep 15, 2022

An interview with Bob Sherriff, Founder of CareerDash

What is the story and inspiration behind starting your company?

My family might be the first family of bootcampers in the United States. Seven years ago, my family started a bootcamp helping veterans transitioning out of the service to launch high-level account executive careers. The success stories were incredible and we ended up selling the organization to a military-focused private equity firm.

Along the way, we came to understand the plight of the military spouse and how difficult it was for them to maintain careers while constantly moving to support their service members. Historically, they’ve been one of the most underemployed demographics in the US because of their constant moving and we knew that business development and recruiting were two careers we could help them launch that would pay well, offer upward mobility, and were highly remote (even pre-COVID). So we created a new bootcamp that focused on training and placing military spouses in those roles called MilSpo Academy and the results were great.

And then the pandemic hit and suddenly there was a demand for remote roles. We started getting outreach from a broader demographic who wanted to make a similar transition. It was at that pivotal moment that we figured out we’d uncovered a formula that could fix the trillion-dollar client-facing skills gap and set out to help all underserved and underrepresented communities launch meaningful careers.

What is the unmet need or challenge that your company is addressing?

Making a career change is incredibly difficult, often expensive, and risky. There are very few good options for individuals who are unhappy with their current path and want to get on to a new one that does not force them to spend a lot of money or time and that can guarantee the outcomes that we do. Our programs provide low-cost, low-risk pathways for adults to successfully launch a new career in a client-facing role that pays well, offers unlimited upward mobility, and can often be done remotely.

What is unique about your approach?

There are a few things that make us unique. Firstly, we offer complete flexibility in our 12-week programs so that the student can learn on their own time. This is important for most of our clientele because most are currently working and/or supporting families while they develop.

The learners are able to do the readings, videos, and assignments on their own time and schedule their live one-on-one coaching based on their own availability.

The most important service we provide is live coaching from best-in-class subject matter experts that work with our students to develop the skills and knowledge that employers are looking for. Each session is an opportunity to reinforce the learning modules as well as role play real-life scenarios our students will encounter on the job. It’s easily our students’ favorite aspect of the program.

They are also guaranteed work experience as part of the program where we give them the opportunity to practice their newly developed skills and make money from working in their prospective roles at CareerDash.

Lastly, our career center is unique with career development specialists who work with students to intensely review their resumes, social profiles, interview prep, and plugging them into our network. We have a whole team around you dedicated to helping you launch your new career.

Finally, we offer these high-outcome programs to our students at a fraction of our nearest competitors and we’re also hyper-focused on our goals to find new and better sources of funding that will lower barriers and help more communities gain access to these careers.

How are you thinking about the impact your product creates?

We’re helping fill a giant gap in the market for open roles with amazing talent. More importantly, we create a more diverse talent pool given that most individuals who choose to go through our program are majority female and from predominantly underrepresented groups.

On an individual level, our programs help people find fulfillment that many struggle to achieve. A new role isn’t just about the work. It’s better pay, a better environment, more flexibility, and more opportunity to move upward.

Our number one focus will always be “Did we maximize our students’ chances of launching and succeeding in their new career”?

What is the next most important milestone for your company?

We’ve had an incredible year so far that doesn’t show any signs of slowing. Our next milestone will be successfully raising a seed round to allow us to put more fuel in this rocket ship.

Additionally, we hope to expand our community college partnership presence such that we have access to federal dollars that will pay for individuals to go through these programs. This would mean we can lower the barriers to more people going through this transition. Alongside that, we’re continually expanding our partnerships with nonprofits to offer scholarships to individuals from disadvantaged backgrounds to get through programs like ours and launch new careers.

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LearnLaunch Fund + Accelerator

LearnLaunch is the leading early-stage edtech startup fund and accelerator.