Career & company transitions
Coaching Through Career & Company Transitions
Find your footing when your role, your company, or your plans change.
Some transitions are ones you’ve worked toward. Others arrive before you’re ready.
A new role, a company sale or shutdown, a career change, or leaving a job can unsettle more than your plans. Even a welcome change can bring uncertainty, loss, or a shift in how you see yourself. Relief and grief can show up together. So can excitement and doubt.
I coach founders and technology leaders through both the decisions in front of them and what the change means to them. You don’t need a new title, a company to run, or a clear plan to begin.
Stepping into a new role
A bigger role can ask you to change how you work before you feel ready. What used to make you effective may now get in your way. You may be leading former peers, managing managers for the first time, or learning the expectations of a new company.
We can work on:
- What to prioritize and where to build trust
- Leading former peers and managing managers
- What to let go of and how to establish your own approach to leadership
There is room to acknowledge what you don’t know while making decisions and taking responsibility.
Selling a company and navigating acquisition
Before a sale, you may be weighing several paths: continuing to operate, changing direction, finding a partner, pursuing an acquisition, or winding down. Those decisions carry consequences for your team, your investors, and you.
An acquisition can look like a finish line from the outside. From the inside, it can be the beginning of a job you haven’t done before. Your team has questions you can’t always answer, decisions involve new people, and you may have more resources and less autonomy.
We can work on:
- Weighing the paths forward and the tradeoffs for you, your team, and your investors
- Preparing for difficult conversations and advocating for your team
- Navigating integration and figuring out what you want your role to become
I co-founded Reaction Commerce and led it through its acquisition by Mailchimp in 2020. I later served as Mailchimp’s Chief Product Officer and Product Advisor. I’ve been a founder responsible for the whole company and a product executive working inside a much larger organization.
In The Identity Shift After Selling Your Company, I share what that transition felt like: the relief, the grief, and learning to lead inside a company I no longer owned.
Our work focuses on your leadership, relationships, and decisions; legal and financial advice belong with your transaction advisors.
“Sara helped me think through each path, understand the tradeoffs, turn ideas into concrete plans, and then actually execute on them. Ultimately, we successfully sold the company.”
Closing a company
Deciding to shut down a company can be one of the hardest decisions a founder makes. You may be trying to distinguish a path worth pursuing from the wish that things could turn out differently, while carrying responsibility for people who have invested their time, money, and trust.
We can work on:
- Examining the options honestly
- Preparing for conversations with your team and stakeholders
- Leading through an ending and letting go of something you’ve built
There is room for that personal experience without rushing to turn it into a lesson or a new venture.
“When it was time to figure out what came next, she helped me see that closing one chapter didn’t have to define me or diminish what I had accomplished. We worked together as I transitioned back into engineering and eventually stepped into a VP of Engineering role.”
Leaving a job and deciding what comes next
Leaving by choice, being laid off, or being terminated can each unsettle your confidence, routines, relationships, and sense of identity. You may need to make practical decisions quickly while still processing what happened.
You might also be ready for a career change without knowing what you want instead. We can work on:
- Making sense of an ending and rebuilding trust in your judgment
- Talking about your experience and deciding what to carry forward or leave behind
- Exploring another executive role, starting something, taking time away, or pursuing different work
A place to think while things are unsettled
You don’t need to have the entire future figured out to take a useful next step.
We might start by separating what is known from what is assumed. Which decisions need attention now? Which can wait? What responsibilities do you need to honor, and whose expectations are you carrying? What matters to you beyond the role you’ve held?
From there, we can work on a conversation, a decision, or an experiment. Some sessions are practical. Others make space for uncertainty, relief, anger, or loss. Often both kinds of work happen in the same conversation.
For a broader sense of what it’s like to work with me, read testimonials from coaching clients.
Work with me
I coach founders and technology leaders through career and company transitions, whether you’re taking on a new role, considering a sale or shutdown, leaving a company, or figuring out what comes next.
If you’re earlier in the company-building journey, see coaching for startup founders. If you’re taking on broader product or design responsibility, see coaching for product and design leaders.
You can also read my thoughts on building trust through one-on-ones and, if you’re stepping into broader product responsibility, choosing where to focus as a CPO.
Read about how coaching works, or schedule a free introductory conversation. We can start with what’s changing and what would make this next chapter feel more intentional.