Working With Jessica: A Guide to Collaboration, Leadership, and Growth

In the startup world, self-authored "working with me" guides have become a useful tool for streamlining collaboration. Originally popularized by Claire Hughes Johnson, former COO of Stripe, these guides help leaders communicate how they operate, their expectations, and their preferred ways of working.

I’ve adapted this idea to create my own version—keeping much of the original structure while adding my own unique perspective. If you’re working with me, here’s what you should know.

My Mindset Pillars

These core beliefs shape how I approach work, decision-making, and leadership. Almost all my behaviors and preferences trace back to these fundamental principles:

Play an Infinite Game

Inspired by James P. Carse’s Finite and Infinite Games and Simon Sinek’s The Infinite Game, I believe success is about longevity, not short-term wins. In an infinite game, the goal is to keep playing—bringing more people in, adapting to challenges, and focusing on sustainable progress. This mindset influences everything from company growth to daily decision-making.

Culture Eats Strategy for Breakfast

A Peter Drucker classic—no matter how strong a strategy is, a weak culture will undermine it. I prioritize building a team dynamic that fosters trust, collaboration, and purpose. A thriving, engaged team is what turns vision into reality.

If You Want to Go Far, Go Together

Speed and sustainability often conflict. While fast growth is tempting, I focus on building something lasting. Rapid scaling without strong foundations leads to instability. I aim for steady, intentional growth that stands the test of time.

Be the Person in the Arena

This phrase, from Theodore Roosevelt’s 1910 speech Citizenship in a Republic, resonates deeply with me. It’s about being actively engaged in the challenges at hand rather than sitting on the sidelines. I respect those who take action, embrace discomfort, and show up fully—especially when things get tough.

How I Work

Building Trusting Teams

I believe in knowing my team beyond just roles and tasks. I want to understand your professional goals, highlight your wins, and foster a space where honest feedback is encouraged. Every campaign should include a reflection session to assess what worked and what didn’t.

Bi-Weekly 1:1s & Learning Sessions

I alternate between 1:1s and collaborative learning sessions. These sessions might involve deep dives into high-performing launches, platform updates, or industry insights. Learning is baked into our rhythm to ensure we’re always growing.

Monday Team Meetings

Each week, we review sprint tasks, address blockers, and set up discussions for cross-team collaboration. These meetings are meant to be efficient, structured, and action-driven.

OKRs & Goal Setting

I prefer structured goal-setting: company-wide objectives inform team objectives, which then guide individual OKRs. We set goals collaboratively, track progress in 1:1s, and evaluate outcomes quarterly. Reflection is key—every success or failure is a learning opportunity.

My Management Style

Collaborative Decision-Making

I love brainstorming, whiteboarding, and talking through ideas. I don’t get stuck on one viewpoint, but this means I can be slow to make decisions without discussion. If you need a quick answer, let me know.

Accountability & Organization

Marketing requires a high level of coordination. I set clear processes and expectations, use task management tools religiously, and expect everyone to communicate progress, blockers, and changes. If a deadline is slipping, I want to hear about it before it’s a problem.

Delegation & Trust

I respect autonomy but expect high communication and collaboration. Responsibility is distributed, and accountability is key. If expectations aren’t clear, ask. If something is blocking your work, communicate. If priorities shift, let’s adjust together.

Data & Discussion

I love data—but data alone doesn’t tell the full story. We need interpretation, discussion, and critical thinking to extract meaningful insights. Asking the right questions is just as important as tracking the right metrics.

Strategic Thinking

I work best when I can see the big picture and break it down into achievable milestones. If a situation shifts, I adapt. If priorities change, I realign. Efficiency and purpose drive my decision-making.

Outside Perspectives

I seek insights from customer feedback, sales conversations, and industry trends. Great ideas often come from unexpected places, so I value diverse perspectives and cross-industry insights.

Communication Preferences

1:1s > Emails & Chats

I prefer face-to-face conversations for complex topics. If something can wait for a 1:1, add it to the agenda.

Emails

• Use email for meeting recaps, quick decisions, and FYIs.
• Assume I read everything, but I’ll only respond if needed. If I owe you a reply, ping me.
• Use FYI in the subject if no response is needed—I’ll do the same.

Chat

• Use for urgent or time-sensitive matters.
• Short pings are fine, but response times vary based on meetings.
• Longer discussions should wait for a 1:1 or a scheduled meeting.

Plans & Projects

I like structured planning. If you have an idea, set up a meeting, bring stakeholders, and be ready to discuss action steps. I’m happy to collaborate, but I appreciate clarity in asks, tasks, and timelines.

Feedback

I love giving and receiving feedback—it’s how we get better. I provide real-time input when needed and hold quarterly review sessions. If you have feedback for me, I welcome it. Open, honest conversations make us all stronger.

Final Thoughts

I care deeply about the people I work with. I want you to feel a sense of purpose, belonging, and growth. My goal is to foster a culture where we challenge, support, and inspire each other.

And finally—I think I’m funny. Hope this guide is helpful, and I look forward to working together! Feel free to contribute to this document and make it even more authorized. 🙂

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