Starting your career at Progressive

Leveraging learnings to progress your career

4 min read

March 2022

Hands typing on laptop keyboard

Over the course of his career, Progressive Manager Dan gained a wealth of experience in various fields from education to working in banking, as well as working for a non-profit. While he enjoyed these various roles, he remained open to ways to further advance his career and opportunities that could potentially fill that gap. Having a friend that worked at Progressive who thought he would be a great fit at the company, he took a leap—considering both the timing and opportunity sufficient to take a risk.

Starting in 2013 as a sales representative in the Customer Relationship Management organization, Dan had an immediate sense that leadership was a route he would be interested in pursuing. Drawing from his background in education, Dan gravitated toward opportunities to help his peers when presented with the opportunity, eventually serving as a peer mentor. Within a year of starting at Progressive, Dan had advanced from being a sales representative to a CRM coach, a role that provides both onboarding and technical assistance for new sales representatives. About 18 months later, he would make another jump forward in his career, stepping into the role of CRM supervisor.

Learning, growing, and vulnerability

When asked what advice he would give to someone looking to either pursue or expand their career at Progressive, Dan stresses the importance of being open to learning. He encourages people to never forget how important each step along the journey is, further stating to “Be appreciative of the opportunity and how that opportunity can grow into other things.” While he admits there was a lot to learn in a short amount of time when he initially started, he stressed that it is never too early to start thinking about the next step along your career journey, stating “If you can prove yourself in your role early, it’s going to build trust that will propel you towards wherever it is you want to go in the company.”

Prior to becoming a coach, Dan remembers how he nearly talked himself out of applying. Ultimately deciding to apply and then being selected for the role, he advises “If you want to move forward in your career, don’t give up on opportunities” and “to always believe in yourself and try.” Reflecting on the skills he brought when he was initially hired along with those he’s gained since, he states “Progressive values all the skill sets we bring and what makes us unique.” Being vulnerable is also a valuable lesson he’s learned and something he advocates others to embrace. He credits his ability to earn buy-in from both those directly reporting to him as well as from peers to his willingness to be vulnerable and share his own past and present challenges. Learn more about Progressive’s culture.

Making an impact

Dan also speaks highly of Progressive’s Employee Resource Groups (ERGs) and the impact his involvement has had, both professionally and personally. Currently serving as a board member of MILNET, an ERG supporting past and present military service members and their families, he views ERGs as a great tool for not only self-development, but also as a conduit to help people connect despite their differences. “Being able to make an impact on others and watch it trickle down” is something Dan takes pride in. As a leader, he’s learned to apply the lessons he’s learned from his experience with ERGs and the diversity, equity, and inclusion space, recognizing that while he can’t change others, he can meet them where they are and build from there.

Now serving as a manager in Commercial Lines, Dan is still driven to continue learning and growing while also bringing others along with him. With a people first mindset, he’s focused on creating an environment where others feel comfortable and can be seen, stating “Asking shows interest, interest conveys respect, and focusing on the person before the task is the best way to develop people.”

Reflecting to before he started, he remembers how Progressive appeared daunting from the outside, especially since he lacked a background in insurance. He encourages those considering a career at Progressive to allow themselves the opportunity to find out if it’s the right fit for them, adding “Progressive has completely changed the quality of my life” and “they’ll give you every opportunity and tool you need to develop.”

Dan Clifford is a manager in Commercial Lines Customer & Agent Servicing at Progressive Insurance. He also serves on the Executive Board of MILNET, an Employee Resource Group focused on supporting current and prior military members and their families. Dan strives to lead from a place of empathy, feeling work/life balance is paramount to the success and sustainability of his team members.

Search careers and apply today

View job openingsCareers login

Join our Talent Network and get updated as new jobs become available.