Lead(H)er Profile - Jen Waldron, SVP of Sales at CareAcademy banner image

Lead(H)er Profile - Jen Waldron, SVP of Sales at CareAcademy

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Our Lead(H)er series features impressive women leaders in the Tech Industry.  In this Q&A, we are featuring  Jen Waldron, SVP of Sales at CareAcademy.

Where did you grow up and what did you want to be when you grew up?

I grew up in a middle-class and primarily white suburb of Boston, MA. I lived in the same house until I left for college. And, I went to public school with largely the same group of people from kindergarten through high school graduation. As early as pre-school, my family tells me that I would run around the school wanting to play ‘king’ and be the leader of the other kids. As a child, I wanted to be president, a veterinarian, and an archeologist … why decide?! 

What did you study in college and what was your first job out of school?

I graduated from Ithaca College during the Great Recession. Like many in the old-millennial generation, I took a bit of an unconventional route to get through college and my first roles after college. 

Right after graduation, during the depths of the recession there were few roles for someone with a bachelors in sociology from a small liberal arts college. I’m a very scrappy, entrepreneurial person and I took the first job that I could find as a housekeeper in a memory care community.  I quickly learned that I really enjoyed working with people who had memory loss.  I asked my supervisor if I could become a Caregiver at that community, they said emphatically, “yes!”  I later learned that senior care companies are almost always understaffed and will hire most people who have the right heart for the work. I was surprised to find that I would end up making less money as a caregiver than I did as a housekeeper. The job was much harder emotionally and physically, and to make matters worse, I received very little training. I was tasked with supporting all personal care needs of 10-13 residents at a time. This experience galvanized my interest in working in the senior care industry and trying to make caregivers' lives better. 

Can you share the details on your career path and what were the critical moments that got you to where you are today?

That first role as a Caregiver was a hugely rewarding and influential experience for me. I really developed a passion for helping other caregivers who care for seniors.  The other experience which made a big impact on me was finding a small company at the time called the Institute for Professional Care Education (IPCed) and which was later known as OnCourse Learning.  I was the 6th employee at an online training company which provided training for caregivers working with seniors. It was an awesome transition and gave me the opportunity to support seniors, caregivers and learn all aspects of the post-acute industry.  

During my time at IPCed and OnCourse Learning, I worked in customer service, compliance/regulations, implementation, and then got into the sales organization and was able to hold all the different sales roles that the company had. When I left OnCourse Learning I was managing the Post-Acute sales organization, a team of up to 14 sales reps and a $7M budget.  Shortly after I left the organization, it was sold for $500M.

What is your current role and responsibilities?

At CareAcademy, I drive our sales and partnerships organization to grow the business. I manage the sales, partnerships and accounts management team members and am responsible for all reps from SDRs through player/coach and top performers. 

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

I didn’t know I would be in this role specifically. But I did always want to be able to do something meaningful that really improves people's lives. I love that what I do helps other people grow their careers, makes them better at their jobs and ultimately improves their lives of older adults. 

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

If you’re interested in a senior leadership role, just know… it’s so much harder than it looks. Every step in my career took longer, required more grit and determination than I ever would have imagined. I also had to take a few big risks to get where I am today. CareAcademy was just a year or so established when I moved my family from Portland, OR to Boston, MA to help grow the organization. Stay determined and when you feel like quitting, take a breath and keep going. You’ll be able to look back and be amazed with how far you’ve gotten.

What are the most important skills that you need to do your job well?

Whenever humanly possible, don’t assume anything!  In regular communication with employees, customers, partners you get so much further when you clarify everything and qualify everything. This philosophy also applies to business decisions, it's worth it to get real data so you’re not left to assumptions.  

What do you find most interesting/rewarding about your work?  What’s most challenging?

As a sales and partnerships leader, I still love the negotiation and closing process with a prospect or partner. Closing a deal still excites me, even after almost 15 years!  Equally as rewarding are the team members who help push forward the goals - I’m delighted and surprised by them on a daily basis. The most challenging is the constant competing priorities of working on a super fast growth product and team. 

What is your proudest professional accomplishment?

There are many! I helped CareAcademy and a previous company establish channel partnerships with the largest and most influential home care franchises. Since joining CareAcademy in Nov 2018, I grew the team and drove 10x ARR growth over that time through direct sales and channel partnerships.  Finally, I helped CareAcademy close the largest contract in company history with a company that’s in the top 11 largest home health organizations nationally.  

Are you involved with any professional organizations outside of the company? Volunteer work?

I’m involved with Pacific Northwest-based Pride Foundation.  Their fund has an enormous direct impact on the lives of people in the LGBTQ community. They give scholarships directly to people from the LGBTQ community along with significant financial support of other grassroots community organizations which help advance equality.


What do you enjoy doing in your free time?

I love to cook and I love home renovation projects. I’ve been told more than once that I make the best chicken pot pie.  And, I love to refinish furniture or other similar projects where I can use a hammer! 

I also love everything about boats. My dad had a couple boats when I was growing up and that got me hooked.

How do you manage stress?

I go for a long walk with my dog at least once a day.  I also find it helpful to literally close my office door at the end of the day and not check work emails or slack after 8pm - it helps me sleep better.

How many cups of coffee do you have in a day?

Usually two, sometimes three though I usually regret the third.

What's one of your favorite places in the Boston/New York area?

My favorite place in the Boston area is Provincetown during the summer.  It’s so lively, fun, sunny, beachy, great lobster rolls - an awesome place to escape for a long weekend!

Any book or podcast recommendations?

On the personal front: I recently listened to Nice White Parents and I found that really interesting.  Professionally: Monetizing Innovation is a great book that really helped me understand what Product does. And, it also helped me think differently about pricing and packaging. 

What advice do you have for recent college graduates?

If you’re anything like me, my college education was great but not very specialized. It takes a lot of determination and grit to dive into being a specialist in a role or an industry. It takes longer than you think to become established in a field, but don’t give up!

About the

CareAcademy provides evidence-based online classes for non-medical professional and family caregivers. 

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