Transitioning from startup to larger companies can be a huge shift in mindset. I made the shift from a 250 person startup (I had worked at from 30 → 250) acquired for $500m to Slack in 2018. Slack was then a pre-IPO company with 1200 employees (grew to 2000 in 18 months).

I struggled! It was significantly different and harder than I expected. In personal conversation with startup friends transitioning to larger companies I’ve given advice on how to handle this better than I did. I decided to type it up for re-use. Like most advice this is a form of nostalgia so YMMV.

For the purposes of this post I’ll assume you are optimizing for executing at a high level in your job and growing while at the company you are joining.

Recognize it’s different

Big companies are fundamentally different + the kinds of people who work there are fundamentally different. Dynamics to be aware of from the beginning:

  1. At a small company you have a reputation, at a large company you have a brand: it’s considered tacky to speak this way, but critical. In a small place people work with you directly and your output. At a large company you have to identify + nurture your brand
  2. Small companies have drama, big companies have politics: in a smaller place the drama is largely about personalities. At a larger place beyond personalities you have deep competing organizational interests. Learning the landscape is critical to build alliances to get your stuff done
  3. Transactional vs relational: there are so many folks at big companies many of the interactions are transactional. If you’re used to the intimacy of smaller companies it can be off putting at first. But it’s natural given the scale. Think about what you can offer and learn who you will need help from!

With those in mind, some tactical advice for a larger company…

Prior to accepting an offer - get the right mandate

In any job change you have the most leverage prior to accepting the offer. This is the time to use it! This is relevant across a number of areas:

  1. Negotiate the role + mandate: most importantly, you need to understand exactly what the role is. What are you going to be paid to get done. You should get a clear sense of (1) what success looks like in the next year, (2) what will you need to be successful, especially from other teams at the company
  2. Negotiate for commitments you need: once you understand your mandate, you need to create a specific list of what you need to be successful. Negotiate this as part of your acceptance of the offer. This could be simple: “I’ll be leading that team of 12 hiring up to 20 people. As part of that I understand I will be able to partner with recruiting, have hiring authority, and have a budget for 2 incremental headcount per quarter for next year.”
  • Note - this is a good test of your potential boss. Do they have the political skill to help secure these commitments for me? Can they clearly communicate what is and isn’t possible? Do you like working with them on this?
  • A tip for this is to jointly create a written doc you agree on before you accept
  1. Get the right compensation: prior to accepting a role you should make sure you are being compensated appropriately. Note, larger companies will have more sophisticated recruiters who are very good at selling you on taking less money. Just don’t. Read this canonical blog post on the topic here. Make sure to do your research on, teamblind, glassdoor, etc…

Prior to starting - pick the right first project

Critical to your brand is delivering on what you commit to. Your first project must be successful. My suggestions for this:

  1. Pick a project that is setup for success: be direct about this with your boss. You want to pick something that is doable. It’s going to be a ton of work to learn how to be effective at a new company. Do something realistically possible but high-impact
  2. One great approach is to pick a domain you already have significant depth in / a project area you’ve executed on at another company before
  3. Make sure that project can be completed in <6 months: get a quick win so you can move on to bigger / more impactful projects
  4. Pick a domain your team can own without help from another organization: don’t start your next role by asking some other team for a favor! Building alignment and understanding politics takes time. Start out by executing on something you can do without alignment or political support
  5. Ideally pick a domain where you can deliver for a key leader/team: if you can deliver something that is an acute need for a leader/team that matters, you’ll build an ally quickly

Building the brand

You’ll start creating your personal brand at a new company before you start. Like any brand - you want to focus on deliverables and communication that are on brand. Some ideas:

  1. Execute at a high level and deliver on your commitments: it is shocking how often people drop the ball at large companies. People don’t follow through. They don’t communicate changes. Following through on commitments and clearly communicating progress, including setbacks, puts you ahead of 90% of people
  2. Create a quick elevator pitch intro: you probably practiced this a lot during the interview process. You’re about to meet dozens of people at the new company. You should be intentional about how you describe yourself. People are going to be thinking ‘is this someone who can help me’
  • This ‘pitch’ should clearly hit skills/experiences that are valuable to this company
  • Don’t be humble. Make sure to communicate the most impressive thing(s) you’ve done
  1. Utilize the formal introduction channels you have: make sure your email introduction, your welcome speech at the team meeting, Slack welcome message all aligned to the brand
  2. Meeting folks before you start: if you have any connections within the company outside of your boss, reach out. Ask about the company culture, values, and company etiquette - are people on-time to meetings, how do people respond to work on vacation, when do people socialize, etc…

Hitting the ground running - understanding politics

  1. Create a mental map of your team’s natural allies, customers, detractors and partners: before even bringing relationships into play, understand that your organization and mandate sits somewhere within the organization. Make sure you understand which teams will be predisposed to support your work
  2. Learn the planning + decision process: make sure to understand the operational cadence of your team + the relevant organizations around you. Figure out who plans on a quarterly basis, when is the regular exec meeting, etc… how issues are escalated (and to who). This will be wildly different than where you came from! Learn this quickly
  3. Meet with junior folks before leaders: always meet more junior folks before meeting with senior folks. They have more time to answer all of your questions. They are also more likely to share political musings early on
  4. Be intentional about meeting everyone: people are busy. Make sure you have a purpose + agenda for any interaction. Either have an ‘ask’ or a ‘give’ - especially when meeting with senior folks

Larger companies - especially fast growing rocketships - can be unbeatable career launchers. I hope this helps with some context on how to maximize the opportunity and think about the transition.