Coaching for startup operations leaders
"A total shift in the way I show up."
I coach operations leaders (Head/Dir/VP Ops, and Chiefs of Staff) inside VC backed, pre-Series B startups who want to embrace the incredible leadership opportunity the role offers, scale as the company scales, and position themselves for their next leadership role.
I've been an exec for 15 years inside fast growing companies, including as Chief of Staff for Yelp Restaurants for 2 years, and as a VC-backed Ops Exec from Seed through Series B for 5 years. I know what it feels like to have hard conversations as you manage peers for the first time (all the interpersonal traps), how to hire, fire, and run layoffs (I once had to lay off my own roommate), and how to scale yourself as the company scales (it's about deep, personal growth).
If you're curious, book some time with me. We'll meet over video, you'll share what's going on, I'll answer questions, and we'll vibe check to see if it feels like a good match. Rather email questions first? Hit me up at shaina.e.anderson@gmail.com.
Who I work with
You're an ops lead for a fast growing, pre-Series B startup, and you want to embrace the incredible leadership opportunity the role offers, scale as the company scales, and position yourself for the next leadership role.
Other than wanting support in reaching your goals, most people start coaching because they feel stuck, blocked, or frustrated with part of their job — or part of how they're showing up.
Below is a sampling of what I regularly hear from people. If this sounds like you, we may be a good fit:
- This startup is a mess. I was promised growth and development, but I'm actually drowning.
- I’ve always wanted to sit at the exec table, but now that I'm here, I'm not sure what my role is.
- I want to develop my own leadership style, but I feel like an imposter.
- My team's growing, and the things I used to own are now being done by a new VP. Feels really weird.
- I'm supposed to lead companywide planning / build a financial forecast / define our hiring plan / fill-in-project-here, and the internet is filled with a bunch of noise. Where do I start?
- I'm scared to be a generalist. It felt really good to be an expert in my old role, and I'm not unsure what I'm actually great at. Is this a real career path?
"I was holding onto a lot of angst, anxiety, fear, and self-doubt. Now, there's a big change in how I'm showing up for my team, my organization, and most importantly myself. I'm more confident, transparent, vulnerable, and thoughtful because of our work."
— Megan, Chief of Staff at At Present
What we'll do
There's two parts to the work we'll do together.
- Our work starts with a 12 week track on leadership, mindfulness, and self reflection. You'll complete reading and writing work each week, and we'll use the lessons from your homework live together, applying what you worked on to whatever challenges you're facing that week. The reading pulls from a large variety of sources to help you connect the dots: from neurolinguistic studies, to work from the world's great writers, to coursework from Stanford Business School.
- After the 12 weeks, we'll continue to meet weekly, but the agenda becomes loose and open, and there's no more required work — you'll bring whatever challenges you're facing, and we'll work through them together.
Starting with the structured 12 weeks is a requirement to working with me. Beyond that, there's no minimum or maximum time that you need to meet, but most people work with me for an average of 18 months.
There's no hiding it: this work takes effort. Internal, emotional effort, and an ask of your time. Each week, we'll meet live for 50 minutes week, and, during the first 12 weeks, you'll need to set aside at least 1 hour for reading and writing homework. But I promise it's worth it effort — People I work with share that this is meaningful, life changing work, both in and out of their day jobs.
Pricing
$200 per session for weekly 50 minute sessions. Most people ask their company to pay, or use some sort of company benefit program to fund it. I'll give you a template to use if you need help making the ask.
What you get:
- Weekly 50 minute 1:1 sessions with me over video call
- To start, a 12 week 1:1 program on leadership, mindfulness, and self reflection, that includes journaling prompts and reading pulled from neurolinguistic studies, the world's greatest writers, and coursework from Stanford Business School alike. This jump starts our work together.
- After the 12 weeks, ongoing, unstructured weekly sessions. This integrates what you learned during the first 12 weeks into your professional work.
- Access to my Resource Library: I've brought together the templates, articles, books, interviews, videos and more that I've used over the years to grow VC backed startups. It's available to you at any time, and we'll reference it regularly during our work.
"Shaina's positivity and warm approach to coaching makes working with her feel like an actually safe place where you can really explore."
My path to coaching
I started with my first coach for the same reasons many people do: I was stuck, blocked, and frustrated with how I was showing up in my life. I was sick of feeling that way, but didn’t know how to move through it.
Professionally, I was in the midst of launching 4 new markets for VC-backed startup Chewse, and working through wild insecurity and imposter syndrome as we were scaling. Chewse was my first high growth startup, and I joined at the Seed Stage: I was hired as a young leader to lead an even younger team. Over the years, I was regularly promoted and given new teams to build, but didn’t have the tools to show up as my whole, authentic self. Inside, I was desperate to succeed and trying my hardest. Outside, I could come across as forceful and dismissive. Oh, and did I mention I was also newly out of a bad, longterm relationship? Woof.
Over the course of a year, my coach cracked me wide open. He helped me tap into new vulnerability and openness through radical self inquiry. It wasn’t magic — it was neuroscience. Through journaling, meditation, and his help, I learned to listen to my body for cues, and how to quiet the noise so my own truth could emerge. I softened. And I saw the impact ripple through both my team at work and my relationships outside of work.
"Shaina's empathy is unmatched and her ability to relate made talking about certain challenges and insecurities much easier."
— Megan, Chief of Staff at At Present