SAFE Stories: Coby Simmons

Coby recently hit the four-year mark at Safewill, and his journey has been anything but typical. We caught up with him to reflect on the pivots, lessons, and growth that have shaped his time here - and what he’s learned about building a career inside a fast-moving startup.

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Q: You've just celebrated 4 years at Safewill! Did you ever imagine your career would take the path it has?

If you had asked me a few years ago what my career path would look like, I don’t think I could have predicted the twists and turns it’s taken. I began at Safewill as the first Sales Development Representative (SDR). I then moved into tech as a Data Engineer, and I’ve now stepped into a Strategy & Operations role. It’s been a dynamic, eye-opening journey, and I'm looking forward to sharing how it all came together - and some lessons I’ve picked up along the way.

Q: What’s driven your growth?

When I joined Safewill, I was still at university studying Data Science and Computer Science, but working as an SDR was my first real shot at contributing to a fast-growing startup. I got to learn the ropes of outbound sales (lots of cold calls and emails), but my manager was also incredibly open to letting me “nerd out” on data projects for the sales team.

I really enjoyed being able to learn on the job and apply the technical skills I was gaining at uni to drive business impact. I was keen to dive deeper into more technical work, which Safewill’s environment made possible. When our CTO came on board and invited me to join the tech team as a Data Engineer, I jumped at the chance.

In short, what drove my growth was a combination of:

Curiosity: I was keen to explore how I could use my data and technical skills in a real-world setting.
Opportunity: Safewill gave me the space to experiment, learn, and fail fast.
Supportive Leadership: My managers recognised my interests and strengths, and they opened doors accordingly.

Over time, I felt the pull to get back closer to the strategic and operational side of the business. I wanted to see how decisions got made, how processes evolved, and how a business truly scales. Again, the leadership team was all-in on helping me navigate that transition. I think that’s what defines Safewill: the willingness to let you carve out your own path.

Q: What skills and mindset shifts helped you pivot?

There have certainly been big changes in ways of working as I’ve moved across different roles in the business.

Moving from Sales to Data to Strategy & Operations is a big change, no question. A few things helped me move successfully between these very different roles:

Adaptability: Whether it’s making cold calls or architecting a data pipeline, you need to stay open-minded about learning the skills required for each task. I never saw pivoting to new tasks as intimidating - just as new learning curves I was excited to tackle.
Ownership Mentality: I treated my projects like they were mine from end to end. In Sales, I owned my outreach. In Data, I owned building the pipeline and visualising insights. Now, in Strategy & Operations, I own my part of the company’s growth and decision-making processes.
Collaboration: Every pivot involved building new relationships and seeking out experts within the company. I was never afraid to say, “I don’t know how to do this - can you show me?” or “I could use a second set of eyes on this problem.” The willingness to learn from people around you is invaluable.

Q: You’ve had a pretty varied journey - what’s stood out the most from working in so many different areas?

The most surprising part is seeing how interconnected every role is within a startup. As an SDR, I thought about how product features or marketing initiatives might affect my pitch. As a Data Engineer, I was extracting and analysing information that the Sales team later used to refine their strategy. Now, in Operations, I combine all those insights - plus the new ones I’ve gleaned from a broader business lens - to help Safewill achieve its key targets.

The most rewarding element has been the holistic perspective I’ve gained. You don’t just understand one piece of the puzzle; you start to see how the entire machine works. And because I’ve worked in those functions, it’s easier to empathise with the challenges and needs of those teams. It helps me drive better decision-making and fosters a deep respect for the cross-functional collaboration that makes Safewill tick.

Q: How did Safewill support you through those role changes?

Safewill’s leadership and managers trusted me to stretch, to grow, and sometimes to figure things out on the fly. When I felt the pull to shift to a more business-focused role, many leaders in the business gave me great advice and helped me make it happen - everyone was supportive in shaping a role that fit my evolving interests.

Q: For others in startups curious about changing paths - what would you tell them?

Ask for Opportunities: If you’re curious about a different function, let people know. Most startups value hungry, proactive team members who want to learn outside their primary job.
Show Initiative: Volunteer for projects that cross your usual boundaries. If you’re in Marketing but want to learn Product, see if you can help with user research or beta testing.
Be Willing to Learn: Switching lanes often means you’ll be a beginner again. Embrace that. It’s refreshing to learn from the ground up and lean on experts around you.

Q: What is your favourite SAFE value and why?

Safewill has four core values: Speed, All-in, Find the Impact, and Elevate. While I resonate with all of them, my favourite is “Find the Impact”.

No matter what role I’ve been in I’ve always asked, “Where can I make the biggest difference right now?” That mindset pushes me to look for immediate ways to add value, whether it’s improving a data process, optimising a sales approach, or thinking about the broader strategy of the business. Finding the impact is about focusing on the work that moves the needle for the business, which also keeps things exciting and meaningful day to day.

My career at Safewill has been anything but linear, and for me that’s been the funnest part. Each pivot has taught me something new about the business - and about myself. If you’re in a startup and itching for change, don’t hesitate to explore different lanes. With the right mindset, curiosity, and supportive environment, you might be surprised at how far you can go.