Today we’d like to introduce you to Jenna Cantwell.
Hi Jenna, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstories.
I am the owner of Cantwell Career Coaching and a former recruiter/staffing manager. I have a passion for carving the pathway for my client’s career growth desires through the deliverance of transformation resume writing, professional branding, and strategic coaching. I’ve had the pleasure of working remotely with 300+ clients nationwide while raising my two amazing and energetic toddlers.
My career journey had a unique start… I graduated from Towson University with a Bachelor’s degree and then I went to work at PBR in Power Plant LIVE! as a bartender. I bartended in the city for a couple of years and then I decided to become a realtor. I passed my exams and joined a brokerage; however, a couple of months later, I received a call from someone I worked with at PBR. Her friend was looking for a talent acquisition specialist at Randstad (a staffing firm) and she thought I would be a good fit for the role.
I am still unsure why she recommended me, having had zero experience in that industry. That being said, something pulled me toward that job and I ended my fresh real estate career to pursue this new endeavor with Randstad. I was quickly promoted to a full lifecycle recruiting role and my unit partner and I were such a power team. We nourished lagging territories, resulting in the incredible transformation from a brand new team into the #2 unit for office and administration at Randstad nationwide. We were sent to Mexico for formal recognition and received the President’s Club award.
Shortly after that career high, I developed a magnetic attraction to really LIVE more and go experience life beyond Maryland. I spontaneously moved 5K+ miles away to Hawaii with friends. I had the absolute best time of my life in Hawaii. I cultivated authentic connections, experienced various cultures, went skydiving on the North Shore, jumped off waterfalls, and did some of the most beautiful hikes in America, including the Kalalau trail on the Napali Coast of Kauai.
While living in Honolulu, I was a corporate recruiter for a reputable local company, Maui Divers Jewelry. I loved this job, I had the freedom to develop hiring and employee retention strategies, execute process improvement ideas, boost employee retention, and promote a positive and growth-minded atmosphere. I worked with 40+ hiring managers throughout all retail stores and corporate departments to fill a high volume of vacancies.
I also met my (now) husband in Hawaii and I became pregnant with our first daughter, ultimately moving us to Seattle to be near his family. I continued working remotely for Maui Divers but something was missing and I was feeling a disconnect as a remote recruiter, no longer being actively involved in the candidate process and the new hire’s success.
I realized the most significant part of my career as a recruiter was helping candidates obtain new roles, more so than helping hiring managers get new employees. To paint a picture… when a company hires an exceptional employee, the company will reap benefits such as increased efficiency, performance, and revenue. However, when a job seeker obtains a new and rewarding career, their entire LIFE can change. I am a big advocate for promoting the benefits that a rewarding career can deliver to your overall life. Your career happiness goes hand-in-hand with your life’s happiness. This ultimately encouraged me to start my own business.
I officially announced the start of Cantwell Career Coaching (CCC) in October 2019. Shortly after, the COVID-19 pandemic struck, and the entire job market as we knew it rapidly changed. People were finally getting the opportunity to work in a remote environment and companies adapted to virtual work. In addition, individuals were being laid off, providing me with the unique opportunity to turn client distress into a blessing. I played an integral part in helping clients take a leap of faith and pursue their passions instead of desperately finding another job they likely wouldn’t be happy in.
I made my way back to the east coast and I currently live on the MD/PA border. My husband and I have two toddlers and life is in a constant state of craziness at all times, but I wouldn’t have it any other way. Working as an entrepreneur gives me the chance to have the best of both worlds: a devoted mother and an ambitious businesswoman.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
Oh, the road has definitely been rocky at times, especially announcing the start of my business right before the pandemic hit. However, my business eventually took off and it continued to grow throughout the past two years. Due to the economy, business is currently a little slower than we’d hoped over the past couple of months. That being said, it’s the perfect time for my virtual assistant and I to strategize, enhance our skills, and target new programs, partnerships, and services/products.
There’s also the struggle of navigating conversations with potential new clients when there are financial objections. I’m not big on the sales aspect of business and I will never force my services on anyone (organic connections are the best!). However, I’m aware of the life-changing benefits a client could gain if they make the investment. Studies have shown that there is a 3X+ better chance of getting your resume noticed if you hire a resume writer. I’ve had countless clients land jobs with significant pay/benefit increases, including salary increases of up to $50K! So, I personally struggle knowing what a client could be missing out on not moving forward, but I don’t always want to voice that too strongly, for fear of sounding too “salesy”
Lastly, for the sake of being 100% vulnerable and providing an absolute truthful response…I struggle daily with personal insecurities, which are tested more than ever as an entrepreneur. Whether you can tell from the pictures or not, I was born with a cleft lip and partial cleft palate. I struggle daily with this, especially in growth phases where I know it is essential to be visible to the public, create video content, and deliver workshops/ live presentations. However, at the end of the day, I am fortunate that this is one of my biggest struggles.
We’ve been impressed with Cantwell Career Coaching, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
We offer a holistic approach to the career fulfillment and career growth processes, including professional branding materials and coaching. I leverage my past staffing/recruiting experience to deliver resumes that are proven to attract desirable hiring managers. We are essentially the storytellers of your career journey.
Current service offerings include:
- Resume Writing: We craft resumes for all levels (entry-level through C-level executives) with a sweet spot for directors and executives. We service professionals from any industry
- Total Packages: Packages include the three essential professional branding materials: resume, cover letter, and LinkedIn profile update
- VIP Package: This is for professionals serious about career growth only. This investment has provided the largest results for clients and the package includes nearly everything you can think of to ‘kick the job search’s ass’ (for lack of better words)
- Client Coaching: Coaching can include interview prep, job search strategies, mock interviews, salary negotiations, job offer process, etc.
- Corporate Partnerships: We partner with corporations to deliver executive resume writing utilized to enhance RFP submittals
- Military Partnerships: We have partnered with military squads to present strategies for transitioning from the military to the civilian world
- Membership: We recently started a Go-Getter membership with a vision of constructing a community of ambitious professionals that support each other throughout anything career-related (not just job seeking)
In the works:
- DIY Kits: We are in the process of creating DIY career kits for professionals who are on a budget or have the drive to do it themselves
- Local Group Collaboration: We are in the early stages of organizing a group of local entrepreneurs in the Baltimore area with the intent of promoting a balanced lifestyle through the effective management of your career, self-love, nutrition, fitness, finances, and relationships
- Additional Partnerships: We plan to expand our services to incorporate more corporate partnerships, including offering career coaching, professional development coaching, and layoff navigation to corporate entities. We also plan to partner with academic institutions, staffing firms, and unemployment offices
- Publications: We plan to get back to basics and write more! We will be launching a CCC blog, as well as partnering with various magazines
What do you like and dislike about the city?
My favorite area of Baltimore is Fells Point, I am a sucker for the cobblestone and the inner harbor (as long as the dirty water doesn’t touch me). I also love watching Ravens games in the city, that type of energy is unmatched
Another pro of the city is the community aspect… watching local entrepreneurs flourish and support one another is simply beautiful and inspiring. Lastly, I would be insane if I did not mention steamed crabs. I love crabs and seafood.
Pricing:
- Resume Transformation $250+
- Total Packages $330+
- VIP Package $975+
- Coaching $150+
Contact Info:
- Website: www.cantwellcareercoaching.com
- Instagram: www.instagram.com/cantwellcareercoaching
- Facebook: www.facebook.com/cantwellcareercoaching
- Twitter: www.twitter.com/CantwellCareers
- Other: www.linkedin.com/in/jenna-cantwell

Image Credits
Jessica Betkey Photography
