A Journey From Home-Kitchen, to VC backed startup, to Fractional GM

Zach Rosenblum
June 14, 2024
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A Journey From Home-Kitchen, to VC backed startup, to Fractional GM

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I’m Zach - an NYC based Fractional GM. For the last four years, I’ve worked with founders across tech, hospitality, and CPG leading sustainable growth strategies & execution. I’m constantly inspired by others' stories through entrepreneurship and how they’ve transformed lemons into lemonade - so here’s my story with some lessons I picked up along the way. 

My Fractional Story

One of my happy places is the kitchen - no, I’m not a chef. I prefer “avid” home-cook. I’ve learned some interesting life lessons in the kitchen: the value of repetitive motions like mincing garlic OR the iterative & creative process of nailing a summer tomato sauce. Kitchens are filled with stories of happy accidents. 

  1. Gooey chocolate chip cookies? Blame (or rather, praise) a resourceful baker who ran out of baking chocolate. 
  2. Crunchy potato chips? Thank a chef from the 1800s who took a customer's complaint a little too seriously. 
  3. Risotto alla Milanese? Chalk it up to a clumsy hand adding saffron to rice. 

These culinary blunders highlight the surprising truth: sometimes the most delicious and iconic dishes are born from mistakes. Similarly, my professional journey has been marked by unexpected lessons and opportunities. 

My journey into fractional work began in July 2020, though back then, I called it a side hustle. At the time, I was working full-time in a role where my team had been drastically cut (COVID times), leaving me with one colleague to handle the work of what had been a ten-person team. Like many, I was working 15-hour days. With burnout looming, I committed to no longer working from dawn to dusk. Yet, I felt I had all this reclaimed time in my day—early mornings and evenings.

My First Fractional Client

Around this time, a friend introduced me to a startup in the hospitality tech space. The company was at an inflection point- strong customer interest but lacked any systems for growth. In a friendly convo with the CEO, I asked a bunch of questions about his biz, I offered some simple suggestions, and thought that was it - nice meeting you. Four weeks later, the CEO reached out, eager to explore working together. Within a week, I set up a single-member LLC, drafted a contract with a statement of work (SOW), and signed my first client. 

Over the next six months, I was embedded in the team - weekly stand ups + retros, I was leading initiatives related to the customer journey, owning key outcomes, and engaged daily with the founding team. Following a discussion about joining full-time, I helped the company reach another milestone: hiring my replacement—a full-time junior team member. As things wound down, I had a hunch I could do this kind of work for more companies - I was eager to find my next client.

The hands-on experience was crucial in shaping my approach to successful client engagements. Here are a few tactical things I learned from client #1 and still remind myself of to this day:

  1. Own my mistakes: I was transparent that this was my first client engagement. My mistakes were  related to wanting to move quickly and deliver results which led to minor friction. 
  2. Communicate early & often: I started a habit to send a concise, weekly recap of outcomes + whats on deck. This ‘paper trail’ helped clarify future expectations and supported alignment. 
  3. Build in flexibility: This meant flexibility into the SOW, final deliverables, and time estimations. I underestimated the time commitment (client #1 was a fixed retainer), and the SOW was too rigid.
  4. Source for Self-Discovery: I thrived on addressing unique challenges and creating tailored strategies for different clients. My diverse background proved highly transferable and essential for early-stage companies.
  5. More Than a Side Hustle: Combining my technical skills like strategy development and execution with interpersonal skills like asking questions, listening, and identifying opportunities allowed me to deliver true fractional work beyond traditional consulting or freelancing. 

What’s a strategy without tactical execution? Kinda like having a killer recipe with no ingredients…Let’s dive into some tactical tips that I’ve learned along the way to standing up a fractional biz.

My Tactical Tips for Fractionals

How I Qualify my Leads 

I’ve identified five client questions that help me qualify the opportunity and set myself up to be successful - Dialogue is the key here:

  1. What outcomes must occur (this year, quarter, etc) to keep the lights on and the dream alive? (aka What are your ‘north star goals’?)
  2. What is currently working well in your business?
  3. What’s the biggest opportunity or area of friction you’re facing?
  4. Do you have a solution(s) in mind for the opportunity or friction?
  5. What’s the best thing you ate or drank recently? (genuinely curious + it’s a compatibility gauge Q)

How I Get My Foot in the Door

My work with clients spans industries such as hospitality, technology, food & bev CPG, and real estate, covering areas from revenue operations and business development to client success and investor relations. This diversity sometimes makes it challenging to succinctly describe what I do. To address this, I productized some of my work to get my foot in the door. 

As a Fractional GM, I’ll productize an initial project like one of the following:

  1. Capture customer or product journeys w/ key systems + tools mapped - a visual roadmap 
  2. Sales flow & CRM audit
  3. Creation or redevelopment of SOPs related to growth initiatives 
  4. Market & competitor analysis + benchmarking 
  5. Project Brief: strategy doc with 360° diligence & proposed execution plan

The initial project lowers the friction to get started, allows me to get into their biz, and demonstrates my experience + value first-hand. From there, I’m able to propose meatier, longer-term ownership of key areas of their business. 

The productization work will look different for everyone (& may not be the same for each client) - think about an output of work you’ll need in order to deliver the desired outcome - could be an audit, strategy report, project brief. What’s most important: close the loop and associate to an outcome a client values, leaving little to interpretation. 

If I Had to Start Over, Here’s What I’d Tell Myself

  1. Develop your business strategy with built-in flexibility to iterate and take your own strengths and advice you give clients and apply it to your own business. Carve out time to work on your own biz.
  2. Consider what makes you special within your industry and/or role of expertise. Be bold and straightforward about that.
  3. Invest in yourself (and your business). Create a scalable toolkit for yourself: tools, playbooks, mentors, and community.

A little something for employers considering fractional hires

  1. Have you had an open role posted for a while? Are current team members carrying the extra weight (or worse—the responsibilities and correlating outcomes are on the shelf)? Consider a fractional team member. 
  2. Have your responsibilities (or anyone on your team) materially changed in the last 12 months? Look away from the crystal ball and guess-timating what you’ll need done for 40 hours a week for 52 weeks a year. Consider a fractional team member, even try before you buy.
  3. Do you have business hypotheses you want to test, which will peel back the onion on your business and provide greater insight into strategic resource planning?  Hire a fractional to rapidly get you to that new checkpoint and make a long-term decision from a place of knowledge.

Tip: Fractional Jobs helps companies navigate fractional hiring, from best practices to talent matching. If you’re interested in exploring a Fractional GM role, hit me up! If you’re interested in another fractional hire, the Fractional Jobs team can help.

To wrap it up (or put it in a doggy bag) - let’s close out with 3 Q/A’s:

What’s the #1 tip (other than Fractional Jobs), for finding new clients?

  1. Definitely your network - all of my clients have come from my network. That also means grow your network - find and follow people in your role, industry leaders, slack communities. 

What’s the one tool I can’t live without?

  1. Airtable… I’ve been using it for years. It’s my CRM, project tracker, to-do list and everything in between.  

What’s the best thing I ate + drank recently? (See what I did there 😜)

  1. Seared tuna nachos (made by yours truly) + a funky but delish combo: harvey’s bristol cream (really just dry sherry) & coconut soda, from Sip & Guzzle.

If you made it this far - thank you! Hope you found it interesting and helpful. Want to chat about my journey, my work, your journey, your work, or what to make for dinner - grab time on my website. Cheers!

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