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 use their professional work as a platform for deep, personal growth.

I've been an operations 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.

 

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Who I work with

You're an ops leader inside 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 use your professional work as a pathway for deep personal growth.

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:

 

 

"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.

  1. 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. 
  2. 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:

 

 

"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 a young leader hired 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. 

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 mindfulness work. 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

 

 

 

 

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