6 Key Takeaways from my first 90 days as Director of People & Culture

Jes Osrow
Thrive Global
Published in
5 min readFeb 11, 2019

120 days ago I joined TodayTix as their inaugural Director of People & Culture. My 90-day review elicited self reflection and key takeaways applicable to anyone in a People Ops role.

1. Learn how to listen without planning for change

While interviewing for this role, it was clear both leadership and the team were committed to codifying the great aspects of the culture but looking for big changes as well — a trait in organizations, but especially startups, that can’t happen soon enough.

TodayTix was searching for a Dir of People & Culture, and I think it says something good about any startup that is committing to this role.

During the interview process I stated that having a 1:1 with every full time employee in the company would be vital to success in my first 90 days. I completed 85% of these conversations, the majority within the first 25 business days. I asked two simple questions: “How can TodayTix improve?” & “What growth is important to you in your role, team, and with the company?” And, if we still had time after those responses, “What is your ‘pie in the sky’ hope for the company as we evolve?”.

Key Takeaway: Most were candid with their input and I was a blank slate for feedback. It was difficult to not try and solve each problem identified. The key role was to listen, make each person feel heard, and to provide assurance that their insights would go into shaping the future of the company.

2. Nothing replaces 1-on-1 conversations

These conversations set the tone for the rapid evolution of people ops, culture, diversity, and development at TodayTix. They provided an effective insight into the wants and needs of the teams. I was able to build a better, more trusted rapport from the first introduction, which has and will continue to serve the employees and the company.

Key Takeaway: These individual conversations created meaning and provide the current import that now drives the outcomes of my work. They remind me of why I’m here and both the people and company objectives I was hired to develop.

3. You can’t let “housekeeping” get in the way (because it will try)

There’s plenty of day-to-day work that keeps me from focusing on and completing the larger, more impactful challenges. It’s a constant mental battle. Do I feel accomplished by checking the Monday.com board? Or if I’m able to sit down and work on a company wide HR survey? More times than not I leave saying ‘what did I actually do today?’

Key Takeaway: Blocking off meeting free time, or removing yourself from the usual desk space isn’t selfish, but key to more long term, impactful work. Working to prioritize what has to be done in the moment and what can wait is essential.

4. What has been completed never feels like enough

My brain doesn’t shut off once I leave work and doesn’t always seem fully charged when I wake up in the morning. The to-do list is neverending (and grew starting on day one). I continually struggle to find balance between the feeling I can do more and satisfaction with what has been completed.

Key Takeaway: Balance is the only way to survive and might be the hardest part of any role, let alone when starting a new role. The constant reminder for me is that ‘I am human. You can only do what humans can do.’

5. Big goals at the onset are key to initial success

I came in guns blazing in my interview process — some goals were general ideas around the impact I wanted to lead, some ideas that should be industry/startup culture standards. From day one the goals were big: revamp the hiring process to be more cohesive and inclusive; modernize company policies; help the team to find and develop a tangible TodayTix culture (for current and future hires); audit hiring platforms, software, and recruiters for better success; create a budget that encompasses culture, employee development and recruitment while reducing cost; among others.

Key Takeaway: These goals are the constant flashing neon sign reminding me of why I’m here and why this role is key to the organization’s success. In the same way you need someone managing technology, or marketing, or partnerships, someone leading people and culture is just as vital. Defined goal setting leads to validation for the work and the size of the goals sets the stage for potential impact.

6. The role isn’t what it seems (and that isn’t a bad thing)

Roles are always more comprehensive than what are advertised (anyone in HR or recruitment understand that intuitively). The Director of People & Culture role has become an archetype in the startup community in name, but not always in practice. This role came with expectations from everyone — and different expectations depending on employee team, level, tenure at the company, or involvement in the creation of the role. My 1:1 conversations made clear the need for someone in this role but also the need for something bigger as the company grows.

Key Takeaway: Very quickly the role became a character to step into and not always someone I was able to embody — imposter syndrome sometimes hit harder than I might like to admit. When taking a step back, this (hopefully) means the role and company will allow for my personal and professional growth. At the same time knowing that sometimes I won’t be able to see the forest for the trees — and that’s okay too.

I am grateful for my own due diligence during the hiring process — gently grilling the CEO during my final interview about how this role can prove successful for all involved — to feel secure in my professional goal to work in an organization primed for growth and change.

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Jes Osrow
Thrive Global

Head of Learning and Organizational Development | Founder @jesosrow | Co-Founder @therisejourney | Diversity Equity Inclusion | Invisible Disabilities