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I'm Sanjay, Senior Director at a Series B Startup. AMA!

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Sanjay Siddhanti (Senior Director of Engineering at AKASA)a year ago

I'm doing a live Ask-Me-Anything (AMA) soon: I'll use this thread to collect questions and will follow up to answer anything we don't cover within the hour.

I'm Sanjay (LinkedIn / Taro) -- I'm a Stanford grad (same as Rahul), where I got a BS in Computer Science and MS in Biomedical Informatics. I've built my entire career in the Bay Area, with the past 5 years at AKASA, an AI healthcare company to help revenue cycle teams.

I'm the Senior Director of Engineering at AKASA. I joined AKASA in 2019 as one of the first employees when we were a seed-stage startup. I originally joined AKASA as an individual contributor, and quickly switched over to management. I built much of the company's early technology as an IC and later as a tech lead / manager. I also started and managed multiple engineering teams at the company, including Platform Engineering, now an org with 20 engineers.

Happy to answer questions about:

  • How engineering leaders think about the role of Senior, Staff, and Principal ICs
  • How and why to transition from IC to management
  • The differences between an Engineering Manager vs Engineering Director
  • How to hire and retain great talent
  • How to succeed in a startup environment

I can also discuss how to introduce effective development processes (code reviews, agile development, postmortems, planning, etc) in early-stage companies and how to evolve these practices as a company grows.

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Discussion

(9 comments)
  • 4
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    Tech Lead/Manager at Meta, Pinterest, Kosei
    a year ago

    You saw AKASA grow from < 10 people to 100s of people. At what point did the company introduce a leveling system for engineers? Who decided the levels that existing engineers would map into?

    • 1
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      Sanjay Siddhanti [OP]
      Senior Director of Engineering at AKASA
      8 months ago

      We introduced a basic leveling system about a year into the company. We didn't spend much time on it, but just wanted to have something concrete to prevent misalignment later down the road. A few of the engineering leaders decided how existing employees mapped to the available levels.

      That leveling guide, while not perfect, has lasted for a few years and we are now in the process of publishing an improved one.

  • 3
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    Senior Software Engineer at Late Stage Startup
    10 months ago
    • Can you share a bit about when and why you transitioned into management? Was that always your goal?
    • In your opinion, when is it appropriate to transition into management, especially if one's goals and strengths align with this career path? For instance, is there a significant difference in transitioning from a Sr Eng to EM as opposed to moving from aStaff to EM?
    • What is the role of the Director level in an Engineering department?
    • As a Senior Director, what expectations do you have for the impact of the Directors/Managers reporting to you? And what impact does your manager and skip-level expect from you?
    • 0
      Profile picture
      Sanjay Siddhanti [OP]
      Senior Director of Engineering at AKASA
      8 months ago
      • Can you share a bit about when and why you transitioned into management? Was that always your goal?

      I transitioned to management after a couple years as a Senior SWE. It wasn't always my goal. In my case it happened organically. I joined the startup as an early engineer. As we gained traction and started hiring, there was a natural need for more managers and I had a lot of business and technical context on what we needed to accomplish.

      In your opinion, when is it appropriate to transition into management, especially if one's goals and strengths align with this career path? For instance, is there a significant difference in transitioning from a Sr Eng to EM as opposed to moving from aStaff to EM?

      It will be an easier transition from the Staff level because you will have stronger technical skills and more experience leading large projects. But, both avenues are appropriate and common. The most important skills is being willing to learn quickly.

  • 2
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    SWE @ Govt
    10 months ago

    As the organisation expands, and as each layer of hierarchy adds a level of abstraction, how do you maintain the core founding mission?

    • 0
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      Sanjay Siddhanti [OP]
      Senior Director of Engineering at AKASA
      8 months ago

      This is critical and there are many common tools for this. Here are some examples:

      • OKRs are a mechanism for the company to publish priorities and goals, and for each team to understand how they contribute to the company's goals. Leaders should be reviewing OKRs of their teams to make sure they align with the company direction
      • Repetition. There should be regular company-wide and department-wide all hands where the priorities and progress are reiterated. Ideally some of these focus on the broader vision, so that the team can understand that they are currently working on just one milestone of a much broader product or ecosystem that the company wants to build over time
      • Positive recognition / rewards for people or teams who further the company's mission. A common example is having a set of company values that are tied to the founding mission, and periodically giving out awards to the employees who best demonstrate those values.
  • 1
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    Senior Software Engineer at Microsoft
    10 months ago

    What are the biggest challenges your org faces in terms of technology development and scaling, and how do you address them?

  • 1
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    Senior Software Engineer at Dialpad
    10 months ago

    How do you assess startup equity at the founding engineer level? Is leaving harder if things don't work out in the long run?

    • 0
      Profile picture
      Sanjay Siddhanti [OP]
      Senior Director of Engineering at AKASA
      8 months ago

      Startup employees should look for significant equity so they can share the upside if the company is successful. However, startup equity is risky and the expected value is higher at big tech companies where the equity is liquid as soon as it vests.

      Leaving a startup as an early employee is a tricky situation. Your startup may be doing well, but it may also be several years away from a liquidity event and early employees must often pay thousands of dollars to exercise their options. The mechanics of AMT tax make this even more complicated because you may be paying tax on gains that are never realized. If your company is doing well, this is a case-by-case decision. Some companies offer a longer exercise window or offer early employees some liquidity via secondary sales. These are valuable avenues for an early employee and should be considered as part of the overall job offer package.