Simply Business
Simply Business Career Growth & Development
Frequently Asked Questions
Career growth at Simply Business gives employees room to move toward work that fits their interests, even when that path reaches beyond the role they started in. Development is presented as a way for employees to deepen their skills while helping the company build simpler insurance experiences for small-business owners.
- Internal mobility across functions: Simply Business supports employees who want to grow into new departments or build nontraditional career paths. An insurance product architect started in sales, moved into product in under a year and later grew into roles with broader responsibility across workflows, team support and product capabilities. He said the company gives employees “freedom to learn about every part of the business,” with managers who keep long-term career growth top of mind.
- Learning built into the work: The company offers formal development through tuition reimbursement, paid certifications and professional development training. Learning also happens through projects, cross-team collaboration and weekly level-up time. One employee noted that dedicated upskilling time helped him build technical skills and understand the product more deeply after entering a field he had not expected to pursue. “Opportunities here are endless,” said one BizOps service desk engineer. “Employees have the ability to shape and grow their careers based on individual goals that they set for themselves.”
- Mentorship and peer support: Simply Business reinforces growth through mentorship and peer learning. An insurance product development specialist said he meets biweekly with a senior software engineer mentor to strengthen his skill set and move closer to his goals. A director of insurer relations also described building a “personal board of directors” for confidential perspective and support, reflecting how employees use both formal and informal networks to grow.
- External signals:
- Career development: Employees surveyed on external review sites describe Simply Business as a workplace where managers invest in employee development, support role growth and encourage people to expand beyond a narrow job description. (Comparably; Indeed)
- Learning environment: External reviews also point to strong peers, collaborative teams and optimism about future opportunities, suggesting a workplace where employees can build skills through both formal support and day-to-day problem-solving. (Comparably; Indeed)
Bottom line: Simply Business offers career growth for employees who want to learn continuously, move across the business and develop with support from managers, mentors and peers.
Simply Business's Candidate Tradeoffs
If you’re weighing whether Simply Business is the right fit, these are the core tradeoffs to consider.
- Simply Business places greater emphasis on employee-driven career ownership than on highly structured, centrally defined career planning processes.
Simply Business Employee Perspectives
Describe your career journey so far. What skills and experiences have you acquired along the way that have helped you get to where you are now?
While my path to engineering didn’t begin with a traditional computer science degree, I’ve embraced learning the technical skills through hands-on experience and self-study. I’m endlessly grateful for the experiences I had beforehand — from my time as a journalist and news anchor to becoming a private pilot and working in public affairs for the British Government.
Discovering software development through Launch Academy was the “aha” moment I’d been searching for. My first role at a small Boston startup was pivotal; being in an environment where I had to dive in and take real ownership rapidly accelerated my growth as an engineer. What I didn’t expect was how much my past would inform my future. My ability to communicate and collaborate comes directly from those earlier chapters. And now, I’m grateful to be at a company that truly prioritizes that same spirit of learning and growth. It’s a powerful reminder that a non-traditional path can be the perfect preparation for a career in tech and in leadership.
What support did you receive from individuals and/or resources that helped you step into a leadership role?
When I think about my path to leadership, it always comes back to the people who championed me. I’m incredibly grateful to my colleagues at Simply Business, who have consistently invested in my growth.
A pivotal moment came when I joined our mentorship program as a mid-level engineer. On the application, I wrote, “I want to be a principal engineer someday,” and they paired me with a principal who became a key guide. He challenged me to think beyond my team’s immediate tasks and to approach problems with a more strategic, high-level perspective. That experience didn’t just build my skills; it fundamentally shifted my mindset and gave me the confidence to pursue a lead role.
Beyond that formal program, great managers have been crucial. Having someone who not only supports your ambitions but actively looks for opportunities to help you grow is invaluable. Their investment in me made all the difference.
How do you encourage other women on your team to become leaders themselves? Are there any stories you can share that showcase how you’ve done this?
For me, encouraging other women to become leaders is about demystifying the journey. It’s crucial to create an environment of psychological safety where they know that setbacks are just part of the process, not a reflection of their potential.
I’ve had the honor of mentoring several more junior engineers and there’s often a moment where a problem feels insurmountable or a mistake seems disastrous. In those moments, my first step isn’t to solve the problem for them. It’s to offer a calm presence and share my own experiences with self-doubt. I’ll say, “I have been exactly where you are. I have felt that same panic. The goal isn’t to be perfect; it’s to be resilient.”
Watching someone’s perspective shift from “I failed” to “I’m learning” is the most rewarding part of my job. I carry that principle into my role as co-lead of our Women’s employee resource group, Empower — creating spaces where women can share challenges openly and build each other up. When we normalize the struggle, we empower each other to lead with confidence.

Simply Business frames career growth as a combination of formal development opportunities, manager support and freedom to explore new paths across the business. Employees describe advancement as both professional and personal, with promotions, leadership training and stretch opportunities helping them build confidence, engagement and long-term investment in their work.
“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.”
Simply Business supports career growth by encouraging employees to explore roles beyond their original function and move toward work that better matches their interests. Employees describe a culture where managers keep development top of mind, provide resources for skill-building and support cross-department mobility.
“If we can make that jump to something that we’re more passionate about, the company encourages it.”
Simply Business Employee Reviews
What People Are Saying About Simply Business
-
Training & Education Access: Learning is listed as a core value with workshops, mentoring, coaching, and support for professional qualifications. Structured offerings include dedicated learning time, internal tech conferences, and funding for external events and certifications.
-
Internal Mobility: Examples highlight lateral moves, secondments, and promote-from-within practices. Feedback suggests employees can shift disciplines and pursue employer-funded leadership courses.
-
Growth Culture: Careers content emphasizes a culture of continuous learning and regular time for skill-building. External recognition for career growth content reinforces visible investment in people programs.
Simply Business's Benefits
Allows employees to pursue continuing education during work hours
Defines roles and sets expectations for success
Encourages knowledge sharing and cross-functional collaboration
Hosts Lunch and Learns
Job training & conferences
Managers hold regular development check-ins
Offers apprenticeship programs
Simply Business has hosted interns and apprentices in office.
Offers mentorship program
SBs mentorship program helps champion your success, provide valuable insights, and supports employees in navigating challenges and seizing opportunities.
Provides continuing education stipend
Provides formal manager training and leadership development
Provides online course subscriptions
Provides opportunities to take on expanding responsibilities
Provides paid industry certifications
Provides personal development training
Provides structured onboarding for new employees
Provides tuition assistance
Provides tuition reimbursement
The Tuition Reimbursement Program at Simply Business has been designed to encourage and support employee development with a maximum reimbursement of $5,250 per employee each year.
Provides virtual coaching services
Supports employee-driven initiatives, not just top-down priorities
Documented path to leadership development
Encourages lateral mobility to expand skills and impact
Promote from within
Provides customized development tracks