Hey everyone, I'm sharing a personal post from my personal blog, which you can find the most up to date version for here. But recopying here for ease :)

Introduction

Hey everyone - this isn’t a lead magnet or some recycled advice post. I wrote this myself, from scratch, zero AI, to help you figure out your career path and break into startups. No catch, no ask - just one small favor: if you know any software engineers, data engineers, or folks who work with SQL, I’d love to chat with them as I build Galaxy (the Cursor for Data teams). Their feedback means the world. If this post was helpful or you want to help me with Galaxy, find me on Linkedin :)

Now, let’s get into it.

Over the course of my career I’ve worked at 3 (now 4) different companies and coached friends, friends of friends, and clients into roles at all types of companies from investment banks to private equity and VC firms, to dozens of startups. I’ve always been a fan of helping others, and have spent hundreds of hours coaching others, networking, and helping others land jobs that they love and are excited about. There is nothing that has brought me more joy than helping people I (and others) care about, finding fulfillment in the workplace.

I’ve put together this document to help document my knowledge and provide it as a resource to aspiring professionals who want to figure out what’s next.

A little on me if this is your first exposure to me:

Co-Founder at Galaxy

Duke 2020, Morgan Stanley Tech IBD, TZP Growth, Unify first Growth / Bizops hire (employee #9)

extremely talented pasta chef, nyc restauranteur, movie enthusiast, marvel adult

https://www.linkedin.com/in/garrettawolfe/

Intro - a quick lesson in finding your way in your career

Since I graduated college I’ve had the fortune of seeing many different industries; investment banking at Morgan Stanley (Tech Group), software investing in growth equity / VC at TZP Group, and most recently Growth / Bizops at a startup called Unify.

When I graduated from college as a CS major I frankly didn't have the initiative to start my career in the Software Development space, it was too foreign to me and the investment banking path was so clearly laid out. Funny enough, when I was an intern at Morgan Stanley I actually thought I would be a career banker because I loved the responsibility and my team (I was wrong however, I didn’t feel fulfilled by the nature of my work).

When I joined Morgan Stanley full time, I was starry eyed at the thought of working in Tech VC. When I joined VC, while it was exciting to some extent, I wanted to move faster and be inspired and build. While this could’ve been a function of the firm I was employed by, I do think there are some fascinating nuances to VC and the industry that pushed me away from investing.

When I joined Unify, for the very first time in my life I felt like I truly was excited to get out of bed everyday and to go to work. I was excited to get to interact with my coworkers in the office, I was excited to learn and help drive outcomes in every part of the business, I was excited to help our team win and grow.

I joined as employee number 9 of Unify back in April of 2024, and at the time of writing this (July 2025, only 16 months later) is now north of 50 people. Things have changed pretty significantly since I joined, and my roles and responsibilities had changed dramatically too by the time I entered my last few weeks at Unify!

I say all of this to emphasize four key points which matter a great deal:

1. Your career journey isn’t linear and it takes time to find what you love doing. You may think you are going to love something and for whatever reason you don’t! Keep searching and trying new things until you nail it, your experiences will compound and allow you to join any organization as a more-informed and and more confident individual. It is never too late to try something new
2. Take a risk! We all can get so easily locked into working at big companies that promise a steady income and a big brand name. I was so exhausted of being a corporate drone and never feeling any purpose or fulfillment during the 8-12 hours I worked each day. Take that leap of faith and do something that makes you excited (and nervous)!
3. I truly believe that the velocity of learning and growth is exponentially faster at smaller organizations, more tech-forward organizations where you have the ability to do and own more than at large firms / with older teams. I have learned more in the last 15 months than in the last 5 years at my other 2 jobs.
4. Things change! Teams grow and shrink, people come and go, competition grows, priorities change, and life happens. Be comfortable with change and the need to adapt and find your path forward.

What is it like working at a startup?

Startups (especially earlier ones) give you an incredible amount of agency. Gone are the days of waiting days for comments on a deck from your boss or the client. Excluding what is expected of you contractually, you are the owner of your own time, the manager of your projects, and the executioner of what you decide you want to do every day.

At startups, there is always something to do, and more commonly - there’s always something that you can add to your plate to help your company win even more. It’s not an easy task, but it’s an intoxicating and exciting feeling that I am beyond grateful to have in my career that has reinvigorated my work days (and even weekends) with a sense of urgency, importance, and desire to do more.

With that out of the way, many of you are here to learn about how to get a role at a startup. But before we jump into it, there are a few things I should warn you of.

1. Working at a startup is hard - the hours are long (I frequently work weekends), the work can be grueling, and the risks are high.
   1. If you want to feel purpose in the workplace and having agency of what you do excites you, it’s all worth it.
2. There is a high degree of risk in working at a startup - the vast majority of startups shutdown, and your equity will be worth nothing.
   1. However, the experience you have and the things you learn are multiples more important than any opportunity cost of working in a typical corporate role.
3. Startups can be emotional - when every day passed is one less day of runway (the time a company has till it has to shutdown), people can get emotional. Startups are high velocity and things can change on a dime.
   1. It is your job to find people who you believe will handle adversity and hardship in a mature and professional way. And for some, this stress / concern is a great channel to motivate yourself to get shit done.

How to get a startup job

Like anything in life, there is no shortcut or cheat code to get a job at a startup. It’s actually quite a complex process and involves quite a bit of thought, planning, and initiative. And I promise, the quantum of effort you put in, will directly impact the quality of the jobs you get.

Looking Inwards

Finding your next gig takes time - you need to be aware of this and understand that finding any gig, let alone one that you would be over the moon about, takes time and effort. When I decided I wanted to go to the startup world, it took me 15 months to nail my role. It took me three months to start getting interviews, another 5 months to start getting offers and another 4 months to really start nailing the selection and interviewing process. By month 15, I was fortunate to have lined up a number of companies who were excited at the prospect to work with me. This isn’t a brag - it takes substantial time and effort. Why does it take so much time?

1. Self awareness and understanding what you want - Any time I chat with someone who wants help figuring out what’s next, the first question I ask them is “what do you want to get out of this move?” The reason I ask this is two fold:
   1. In order to effectively and efficiently look for something that you want, you need to identify the criteria that make it a qualified opportunity! If you don’t know what it is, you’ll probably never find it!
   2. In order to get a job, you need to be able to articulate what you are looking for in a company to a founder or hiring manager, what you want to do day to day, and why - and you need to convince them of it! Humans are terrible liars and the less conviction you have in yourself and what you want, the more obvious it will be in interviews. The questions you need to ask yourself are:

What do I want?

1. What industry do I want this company to be within?
   1. Tons of people say they don’t care what their employer does, but if we’re working at minimum 40 hours week (definitely north of 70), why wouldn’t you care! We want everyone to be excited about what they do every day and the mission the company has.
   2. Answer this question by selecting areas that are interesting / exciting to you.
2. What stage company do I want to work at?
   1. The earlier the company, the more risk, the more reward, the more casual, the longer the hours, but the more agency you will have.
   2. You can answer this question typically by looking internally and asking how much risk you want to take, what your working style is, and how fast you want to move.
3. What role do I want to have at the company? What do I want to work on day to day?
   1. The roles and responsibilities of people at a company can vary quite significantly. There are differing qualifications by role, and what you will do will vary as well.
   2. Answer this question by reflecting on your background and find a combination of what you want to do and what you’re qualified to do.
4. What time horizon am I looking at?
   1. Based on where you are in your life you may be looking for different things? Are you young and hungry? Do you need to start a family soon? Do you have kids already? Crazy, but this is important to think about.
5. Cherries on Top: Once you nail the above categories, you can also optimize for a few more factors
   1. Locale - where do I want to work? Am i comfortable moving?
   2. Working style - are you the type of person who likes to be told what to do and then you go and do it? Do you like to work on projects solo and be your own manager?
   3. Work Flexibility - Do you want to work in office 5 days a week or have a mix of remote and in office? Learning is much faster in real life. Some startups now expect 6 or more days in office!
   4. Backers / Investors - the best companies and the best people are typically (not always) backed by the best venture capital firms. This tends to be a good signal for you to explore as you research companies
   5. Perks - self explanatory
   6. Pay - also self explanatory but will note that you should not expect to be paid tons at Pre Series D companies in IC roles.

Looking Outwards

Ok, now that you’ve done some introspection and self discovery, you probably have some solid answers to the above questions! With this set of data, we can actually go out and into the world and try to find what would excite you!

Refine your resume

This is more nuanced but you should try to rework your resume to emphasize your skills that promote your

• Cross functional projects
• Side-gigs / side hustles that show initiative
• Areas where you’ve worked on projects that have tangible ROI / benefit to your organization
• Personality and hard-working nature
• Ability to be an individual contributor and a manager / coach

Emphasize / Create your brand

• Emphasize your personal brand if you have one or create one if you don’t! These things show initiative outside work and your ability to leverage your network. Things like starting a blog, building a portfolio, generating a following. This is what led me to start NextRound - to build my interest in startups :)

Tap your network (absolutely critical)

Before and during your search, reach out to friends, colleagues, and people in your network that may be able to help guide you through your search and learn more about

1. the roles you’re interested in
2. the size of companies you’re interested in
3. the industries you’re interested in
4. the types of problems you might be able to help solve
5. what they have learned and what you should expect

Build a list of companies

Use resources like Crunchbase, LinkedIn, Pitchbook, SourceScrub, Harmonic, Apollo, ZoomInfo, or any company data tool to create a list based on the criteria above. You can even use Perplexity or the LLMs now. You can add filters for

1. Size (# of employees)
2. Stage (stage of funding)
3. Industry
4. HQ location
5. Founding Year
6. Investors
7. Last Funding Round

Empirically, if you enter these filters into Crunchbase as I just did, we only get 27 results!!!!!

When you do the same search but anchor to San Fran, you only get 19!!!!!!

Lucky for you, this is your total addressable market, or TAM, of companies that meet your search criteria. The fact that its sub 50 is actually a good thing - it means you can spend time hand-researching each one and determining which you are the most excited about.

It’s time to do your own outreach!

Many friends and colleagues I’ve advised like to passively search for jobs by applying to job application they see on LinkedIn. I personally guarantee that you will almost never get an epic job via this type of initiative, and it will also take considerably longer. The hottest most exciting companies out there have dozens of people reaching out to the founders, putting together crazy case studies, or showing interest in bizarre ways. They also have headhunters / or recruiters working on their behalf, so you need to do your own outreach and make yourself stand out while doing so.

1. Use LinkedIn to find the relevant people to reach out to at a company and message them.
2. Use tools like Apollo or others (leveraging free plans) to find peoples work or personal emails to send them emails
3. In sending emails, find the messaging that works for you sharing
   1. your background
   2. why you’re interested in / excited by the company
   3. how you think you can help
4. Be sure to follow up and try to break in!
5. I recommend exploring using a Notion / Airtable / Hubspot / Google Sheets for keeping track of companies / outreach activities (all free tiers)
6. While I do recommend writing emails by hand to make it personal and stand out, I recommend using Hubspot or similar tools to use templatized emails (that you can further customize).

What do I need to know to succeed?

Once you’ve gotten in touch with the team and have shared your interest, the job is relatively simple from there, it’s all about working on your story and why you’re a good fit, conveying what you want to do, and managing a interview process.

1. Your story / fit
   1. Why are you interested in this company?
   2. Why does your background make you a good fit for this company and a good fit for this role?
2. What do you want to do?
   1. What do you actually want to do day to day?
      1. This is extremely difficult to determine without startup experience, but having ideas here is the best way to differentiate yourself. No founder wants to work with someone who “has no preference / doesn’t know what they want to do” or “wants to strategically tackle problems in a cross-functional manner” (i.e. they are being vague because they don’t know).
   2. What projects would you want to work on?
   3. What problems do you imagine this company has and how you would solve them?
      1. Once you can answer this, you are in a very good place.
3. Managing the interview process
   1. Having a perfect resume
   2. Sending thank you emails
   3. Being outgoing and following up, showing consistency
   4. Create a list of thoughtful questions to ask founders and hiring managers (e.g., questions about company vision, culture, runway, and growth plans).
   5. Negotiation
      1. Far more nuanced but worth exploring typical comp / equity ranges associated with different roles and different stage companies
   6. Getting answers to questions you should do your homework on
      1. How much money are we burning? How much runway do we have?
      2. What does my trajectory at this company look like? When will I be promoted if I perform?

Things to be cautious of

• Founders who are too young
  • Being a founder is hard - you want people who have a certain degree of maturity and experience working with and managing other people.
• Companies that have declining headcount growth (excluding the effect of AI)
  • Companies whose growth has slowed is typically an indicator of poor performance and company growth / health
  • Of course AI has made teams more efficient so something to weigh here
• Companies that have high degree of legal / market risk
  • It’s important to be cautious of companies that have inherently high degree of risk such as sectors that are relatively novel, involve lots of legislation, or are dangerous in nature. Examples of this may refer to crypto, AI (to some extent), drugs, etc.
• Companies that have questionable degrees of market traction / product market fit
• Companies that have an intensely competitive competitive landscape

Appendix

Different stages of companies

In the below table, I try to share a rough breakdown of companies by stage, specifically for the technology / software space. This is not representative of every company in every space.

• Pre-Seed
  • All ideation and product discovery, focused on building
  • <5 people
  • No hierarchy
• Seed
  • Focused on building and exploring how to sell
  • 5-15 people
  • Still no hierarchy
• Series A
  • Scaling GTM and product development
  • 15-30 people
  • Early signs of specialization / teams forming
• Series B
  • Hiring Org leaders and scaling teams
  • 30-60 people
  • Formal reporting begins
• Series B - Pre-IPO
  • Growing explosively, becoming corporate
  • 60-2K people
  • Full blown orgs
• Post-IPO
  • Full blown bureaucracy
  • 2K+ people
  • Ooooof

Rough classification of roles

In the below table, I try to share a rough breakdown of roles at a company, specifically for people with Business / Consulting / Finance experience (backgrounds like myself). This is not representative of every industry and is limited to my experience.

• Account Executive (AE) | Sales Org
  • Alternative Names
    • Growth (at young companies)
  • Account executives exist to manage and close deals that are generated by new business teams in the form of pipeline. They are responsible for closing a certain amount of revenue each month. They receive less equity because they are typically paid tons in commission
  • Skills
    • Managing relationships, Multithreading, Owning a quota, People skills, Selling
  • Equity
    • Very little
• Sales Development Representative (SDR) | Sales Org
  • Alternative Names
    • Business Development Rep (BDR), New Business Rep (NBR)
  • Sales development representatives exist to generate new leads for Account Execs via cold calling and emailing. They are responsible for generating a certain number of new leads per month. They receive less equity because they are compensated well on leads generated. While SDRs are one of the most important roles at a company, they tend to be considered more junior in nature.
  • Skills
    • Cold calling, Cold emailing, Owning a quota
  • Equity
    • Very little
• Business Operations | Operations Org
  • Alternative Names
    • Bizops
  • Bizops was where I started at Unify. In this role, you’re a jack of all trades, juggling things like company finances, revops / CRM work, sales enablement, post sales C-suite assistance, case studies, event organization, and everything inbetween
  • Skills
    • Cross functional, Jack of all trades, Managing finances, Revops work, Sales enablement
  • Equity
    • Slightly more
• Growth
  • Alternative Names
    • GTM Engineer, Growth Marketer, Growth Specialist, Growth Operations
  • Growth is a relatively newer role which refers to people who work on strategic projects that generate pipeline. Think of Growth as a super ninja version of SDRs that focus on building projects across automated outbound, partnerships, paid traffic, marketing, inbound, and more.
  • Skills
    • Deep understanding of Revops, Systems thinker, Works well with new tech
  • Equity
    • Can vary based on cash comp
• Customer Success
  • Alternative Names | Post Sales Org
    • Post-Sales, Growth Strategist,
  • Customer success is a post sales role that involves helping with onboarding, getting customers to success, triaging bugs, and more.
  • Skills
    • Patience and tolerance,Reporting and solving customer bugs,Working with customers
  • Equity
    • Slightly more
• Engineering
• Design

Thanks for reading, you can reach me here:

• Linkedin
• Email
• Twitter
• and of course follow Galaxy