At Simply Business, Diverse Career Paths Are Encouraged 

Inside the digital insurance brokerage’s culture of support, exploration, and experimentation. 

Written by Taylor Rose
Published on Jun. 16, 2025
A group of four Simply Business employees meet around a conference table in front of sunny windows.
Photo: Simply Business
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 When Jaci Patton attended her first company-wide meeting at Simply Business, she was in for a shock. 

“Shortly into the meeting, people started shouting out ideas for new tactics we should try or people we should meet with in the industry to accelerate our growth,” Patton said. 

Patton had expected what a lot of tech professionals probably would: to listen to a formal presentation for an hour, then head back to work. 

“It was totally unexpected to me,” she said. “It made me quickly realize that the way I’d contribute at the company likely wasn’t just going to be preparing spreadsheets and reconciling numbers.” 

Since then, Patton has indeed accomplished a lot more than running pivot tables in Excel. Not only was she promoted from Financial Planning and Analysis Manager to the Director of Financial Planning and Analysis, but Simply Business also footed the bill for her to attend a weeklong INSEAD course on “High Impact Leadership” in France. Fast forward to five years later and Patton found herself getting applauded at a similar all-hands meeting, where she was recognized as a “U.S. Inspiring Leader.” 

“As someone who didn’t entirely see myself as a leader prior to that, winning that award gave me a lot of confidence that I must be doing something right,” Patton added. 

In big ways and small, internal mobility is woven into the fabric of Simply Business’s company culture.

What does Simply Business do? 

Simply Business is a digital insurance brokerage that allows small business owners to find and buy the insurance they need.

 

A Culture of Support and Empowerment

Simply Business has built a culture of encouraging employees to explore new career interests and supporting them while they do it. Formal support at the company looks like tuition reimbursement, payment for certifications and professional development training, and programs for mentorship, apprenticeship and internship opportunities. Informal support shows up in moments like cross-functional collaboration with another team on a tricky project or managers who encourage career pivots. 

Even early on in Sarah Kac’s career at Simply Business, first as a Relationship Manager and now the Director of Insurer Relations, she saw the growing company encourage folks to explore new roles and advancement. 

“Observing individuals taking on diverse responsibilities and contributing to projects beyond their core roles indicated a willingness to offer employees opportunities to broaden their skills and experience,” Kac said. “The welcoming and exploratory culture around new ideas gave me the impression that proactive individuals — who identified improvements or new initiatives — would be supported and potentially empowered to lead them.” 

Since joining the company, Kac has also attended the INSEAD leadership course, which helped her grow professionally in strategic thinking, communication, collaboration and team development. Now, as a leader in the company, Kac is helping her team pursue their own professional goals. 

“These professional achievements have not only advanced my career but have also contributed to my personal growth, making me feel more confident, engaged, satisfied, motivated, and deeply invested in the work I do and the people I work with,” Kac said.  

Two Simply Business employees chat in front of a green background.
Photo: Simply Business 

Today, Kac has what she calls her own ‘personal board of directors,’ connections that have helped Kac combat imposter syndrome. 

“This concept, which deeply resonated with me after hearing about it at a women’s leadership conference, offers a confidential forum to discuss challenges, gain varied perspectives, and test new ideas,” Kac explained. Her board of directors includes professionals both inside and out of her field whom she considers dedicated sources of encouragement and support.

The culture of empowerment, exploration and experimentation at Simply Business impacts everyone, Kac said. 

“The environment cultivates a sense of psychological safety, where individuals feel comfortable sharing their talents and voicing their opinions without fear of negative repercussions or infringing on others’ roles,” Kac said. 

A group of Simply Business employees meet around a table in an open office space.
Photo: Simply Business 

 

‘Nurturing Diverse Skill Sets And Facilitating Internal Mobility’

A lot of tech workers fear automation replacing them at work, but Drew Curd, Security Engineering Lead, replaced himself with automation.  

“Initially hired for a performance engineering role at Simply Business, I quickly automated most of the tasks I was hired for,” Curd shared.

But the culture of exploration and career diversity at Simply Business meant that Curd wasn’t punished or told that his role was now redundant due to automation. Instead, Curd talked with his manager and the Head of Service and Operations about transitioning to work with the DevOps team. Since then, Curd joined the team as a Senior Engineer and even moved teams again to join Information Security as a Security Engineering Lead. 

“This opportunity to expand beyond my original responsibilities solidified my belief that Simply Business is an environment where I can pursue technical growth and explore diverse roles,” Curd said.

“Simply Business fosters an environment that actively encourages employees to delve into areas of interest, even without prior formal training,” Curd said. “This commitment manifests through opportunities for lateral movement within the organization, providing a valuable platform for experimentation, continuous learning and professional development.” 

Simply Business’s Professional Development Perks 

  • Continuing education stipend
  • Customized development tracks
  • Job training & conferences
  • Mentorship program
  • Online course subscriptions available
  • Paid industry certifications
  • Promote-from-within
  • Lunch-and-learns
  • Continuing education available during work hours
  • Tuition reimbursement
  • Personal development training
  • Virtual coaching services
  • Apprenticeship programs

During his time at Simply Business, Curd said many colleagues have contributed to his professional development. His first manager pushed him to embrace new opportunities and venture into unfamiliar technical domains, while another manager supported many of Curd’s innovative ideas. 

“He granted me the autonomy to experiment, learn from failures, and develop independently,” Curd said, adding that many of his peers have also served as technical sparring partners, constantly challenging one another to try new things and always level up.

“Simply Business prioritizes internal mobility, offering opportunities to existing employees,” Curd said. “This has cultivated a culture of career diversity, with team members bringing varied experiences across the organization.”

Responses have been edited for length and clarity. Images provided by Shutterstock and listed companies.