Career Paths for Startup Employees – Addressing the Need with a Two-Track System

by Mar 18, 2021Talent Management

Why is management career track the only way for people to truly move up? I am not the only one who lost gifted salespeople, marketers, engineers, and other subject matter experts to “management.” Some burned out and left companies (often for the non-management roles), some stagnated in a management role, and others left the craft altogether. The makers, innovators, and passionate craftspeople deserve a career track that reflects their strengths. Let’s ask ourselves the questions:

  • Is an engineer, who becomes a subject matter expert, puts together meetups, speaks at specialized events, promotes the company at conferences, publishes papers, contributes to patents and public projects is any less critical than the CTO?
  • Is someone, who continuously architects core features one after another but does not want to manage people, less valuable than the Head of Product?
  • How about a salesperson, who rescues quarter after quarter and pulls up the entire team with their deals? Are they less valuable to us than the Head of Sales?

The answer to me, and a rapidly increasing number of founders I speak with, is a solid No. Expert makers/craftspeople have as much value and importance to us as our leaders. Ten years ago, that was not the case, so this change excites me a lot!

The solution is at least a two-track/two-path system. How you structure it will be unique to the organization, culture, people, and goals. This post aims to help you think about how you could go about it, not provide you with the recipe for how to do it. This is also one of the “live posts” I am editing and updating as my thinking evolves with new lessons learned. When you start working on the system, you may discover you already have elements of it. You may find functional area leaders already have done structuring their teams behind the scenes with “shadow HR.”

Context matters

We are building and evolving a career path system to address the diversity of talent on our teams. Our context is to make everyone flourish on our teams by allowing them to contribute from their strength. We want our people to be themselves.

High-level tenets

Recognize a professional can bring high value to the company without many (any) people reporting to them.
Craftsmanship and subject matter expertise have the value and multiplier effect on the business comparable to excellent management and leadership.
We determine fitness for levels in each track by measurable, verifiable, and clear achievements. Education and tenure are not those measures.
A person can switch tracks since circumstances, priorities, and motivations change, which we should accommodate. Optionality breeds creativity.

6+ levels

I have observed two-track system doesn’t work well without at least six levels in each. In my experience, breakdown usually happened when we started recruiting outsiders for higher levels. 6+ levels provide the necessary differentiation and recognition. The company may not have employees at each level, which is OK since levels are not for the org-chart.

The tracks


We focus on skills like the ability to organize, enable, mentor, manage, get buy-in from an ever-increasing number of colleagues. Notice introversion or extroversion have no bearing here. The ability to deliver results for the business in managerial functions is. The management track is for those good at procuring for the team’s needs, those willing to put themselves in the line of fire when things go wrong. In general, I have and seen other companies use the following levels: Apprentice (or Intern) -> Associate -> Manager -> Director -> Head of (or VP)-> CxO.


We are focusing on the fluency/depth of the person. T and π personas. With each level, they become more autonomous, and at the same time, their expertise starts creating a gravitational field of knowledge. Every Staff level professional I have worked with made me feel smarter even after a coffee conversation. And those at Apprentice level display incredible curiosity and drive to learn. Levels I have used across most functional areas were: Apprentice->Junior->Mid->Senior->Lead->Staff


There are many variables to consider here. The last couple of times I had to develop compensation packages for the two-track system, I pulled data from Radford, AdvancedHR, Payscale, Glassdoor, AngelList Talent, and usually had access to pay info from friends with access to VC data. Having the levels and exact requirements for them made it much easier to develop or update the plans. The hardest part was deciding how we will deal with employees located in different cities, states, or countries we did not have formal offices. Then we decided on which percentile of the market compensation we will stick to and committed to it across-the-board. The important part is being consistent and highly-disciplined.
Note: it is not out of line, in a two-track system, to see an expert track person receiving higher compensation than the most senior manager of the team.

Timing of raises, promotions, and compensation adjustment

You can either do “as requirements met” timing (this one was my favorite) or stick to a schedule of, say, March 1 and October 1. I tend to advocate for my favorite one because I like my teams in high cadence. It depends on your company culture and policies. There is no correct answer here, as long as it is suitable for your team.

“Up or out” or “let them be”?

Younger me would be all over the “up or out” from Deloitte and Arthur Anderson years. Not everyone wants to hit the cadence of development a highly competitive colleague may. Not everyone has the luxury of time to continuously educate themselves and move up. And that is OK. Compassionate leadership means you make room for everyone as long as they deliver on agreed-upon expectations.
For example, if your mid-level accountant has no interest in moving up and consistently meets expectations and produces, leave them be, let them grow at their own pace. The company is taken care of, and so are they.

Parting thought

Career development and growth are the responsibility of the professional. Adults are responsible for themselves. But learning does not happen in a vacuum, and the company benefits from the growth. Hence, the leadership team’s role is to provide the opportunity, tools, and support for growth.

Image credit: Ted McGrath

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