Write A Stellar Resume As A Software Engineer [Part 15] - Ordering

Everyone reads top-down, and this applies to resumes as well. This means that you need to be deliberate about what goes first and the overall order of your resume's content. This lesson teaches you:

- The core principle behind proper resume ordering
- The best resume section order for the vast majority of engineers
- The best resume section order for engineers who have 0 work experience (college students, bootcampers, self-taught developers)

Write A Stellar Resume As A Software Engineer [Part 12] - Esoteric Terms

As a software engineer, it is absolutely critical for you to write a resume that is incredibly easy to understand, particularly for the recruiter (who, as a reminder, is a non-technical person). Unfortunately, it's very easy for engineers to get this wrong. This lesson teaches you:

- Why engineers often unintentionally make their resumes near impossible to understand
- What esoteric terms are and the categories they fall into
- How to get rid of esoteric terms from your resume with an in-depth example

Grow From Mid-Level To Senior Engineer [Part 15] - What's The Plan?

The best engineers act proactively instead of reactively, and this is critical for successful project execution. This lesson teaches you:

- The evolution in ownership of a project when it comes to a mid-level engineer vs. a senior engineer
- What a good project plan looks like

Check out the system design course for an excellent example of a master spec document: [\[Course\] Frontend System Design Masterclass - Building Playlists](https://www.jointaro.com/course/frontend-system-design-masterclass-building-playlists/)

Negotiation Course: Reneging An Offer

Backing out after accepting an offer (*"reneging on the offer"*) is unfortunate but happens more frequently than you think. Imagine that you accepted a job offer, but two weeks later, you finally get an offer from another company that is better in every way. What do you do?

First, prevention is the best cure: try to get all the offers around the same time.

If the timing mismatch is unavoidable, you should do what’s best for you: don’t worry too much about the company.

In the US, employment is at-will, so there’s nothing legally preventing you from joining. Of course, you may have to give back any kind of signing bonus.

There may be reputational damage: talk about why the opportunity is incredibly unique and you hope to work with them again. Reneging on a large company is not as big a deal compared to a startup.

Negotiation Course: Recruiter Case Study: Insights From An Ex-Meta Recruiter

This was a conversation with a recruiter who spent several years as a recruiter at Facebook (Meta) and Pinterest. 

- The tactic of *"I will sign the offer if you meet me here"* is **effective if it's sincere**. You should be prepared to explore/defend various options around other ways the company could compel you to sign the offer.
- Exploding offers are almost always fake. Recruiters know that "**time kills all deals**" so they want to close candidates quickly. However, as a candidate, you can and should push back on an arbitrary deadline. Ask why the timing constraint exists and share why you need more time.
- Be graceful when you turn down a company's job offer. This recruiter would frequently be able to hire candidates several years later who had received an offer if they kept the relationship alive.

Negotiation Course: What's Best To Negotiate

As you think about what components in the offer to negotiate, you should consider: 

1. **Where do you have the most alignment with the company?** For example, reducing the "clawback period" for your signing bonus from 1 year to 3 months is unaligned since the company wants to incentivize you to stick around beyond 3 months. On the other hand, doubling your equity package is more aligned, since your comp will go up if the company does well.
2. **Where can the recruiter best help you?** Generally, a recruiter is powerless to adjust things like 401(k) match or performance bonuses since they're standardized across the company. However, recruiters are able to adjust salary or equity, especially if you are willing to make trade-offs between them.

Another dimension to consider is that equity is riskier than salary, so, therefore, it should translate to a higher potential reward. Stock options and RSUs fluctuate in value based on the market.

If you're ok with the risk tolerance, you are likely able to get more equity vs salary, e.g. increase your equity $20K/year vs salary $5K/year. This is an **obviously** good trade for a Big Tech (FAANG) company, which will have a fairly stable stock price.

Negotiation Course: When Should You Negotiate? And When Should You Not?

Negotiation makes the most sense for "high-leverage jobs" like software engineering or most other jobs in tech. An example of a low-leverage job would be to stock shelves in a grocery store or drive a taxi in NYC. The difference between the best and average worker in those fields is not that large. But in engineering, the difference in output for the best vs the average can easily be 10x or 100x.

Within the high-leverage category, there are jobs that have many comparable data points (e.g., junior or mid-level engineer) and those that are bespoke because they're rare/senior at the company, e.g., executive level or senior engineering leads.

Negotiation makes less sense for jobs that are purely stepping stones, or those that are time-bound. The classic example here is for internships. A good litmus test is if you know anyone who has ever negotiated that offer, e.g. no one at Stanford ever negotiated the summer research pay.

Finally, negotiation does not make sense if you already accepted the offer at a lower number.

Nail Your Promotion As A Software Engineer [Part 29] - The Step-By-Step Plan

Here's the step-by-step plan if you want it for your notes:

### Find A Good Team

- **Engineering manager has a track record getting engineers promoted**
- Teammates 1 level above you to learn from
- Teammates more junior than you to lead
- Team isn’t overloaded with engineers at your level
- Team isn’t overloaded with engineers at next level

To learn about finding a quality engineering manager: [\[Masterclass\] What Software Engineers Should Look For In Their Engineering Manager](https://www.jointaro.com/lesson/oeY7ncZhzJ5NO6dij5e7/masterclass-what-software-engineers-should-look-for-in-their-engineering-manager/)

### Establish Yourself As A High Performer

- **Build a strong, honest relationship with your engineering manager**
- Identify core peers and add value to them to make them like you
- Develop a consistent track record shipping with velocity and quality
- Look for opportunities to expand scope of assigned projects
- Be creative and brainstorm new project ideas

To learn how to build trust quickly: [\[Course\] Effective Communication For Engineers](https://www.jointaro.com/course/effective-communication-for-engineers/)

### Clarify Expectations And Gaps

- **Write a promotion plan with as much clarity as possible**
- Have that honest, deliberate conversation with your manager
- Observe engineers at the next level to understand the delta
- Break down your weaknesses across engineering axes
- Don’t get jealous of more senior peers

### Execute And Grow

- **Make sure to check in on and maintain your expectations plan**
- Publicly document and share your wins
- Go through your gaps 1 by 1 and patch them up
- Be hungry for feedback and learn from mistakes
- Amp it up in the final quarter before review

To learn how to get constructive feedback: [This Is How You Get Feedback - Making The Process Smooth](https://www.jointaro.com/lesson/aGuxjGbFjYb34ofhRxjs/this-is-how-you-get-feedback-making-the-process-smooth/?playlistId=llknt3sHtV4xmhDThKOx)

### Go Through Performance Review

- **Thoroughly go through your promotion plan and make sure it’s all addressed**
- Compile artifacts from your brag journal, launch posts, and other sources
- Link as much evidence as you possibly can
- Request targeted feedback from core peers
- Share self-review with manager beforehand

Nail Your Promotion As A Software Engineer [Part 9] - You Need More Senior Teammates

As a software engineer, it can be confusing on what's actually needed to get to the next level. Having more senior teammates helps tremendously with that. This lesson teaches you:

- Why more senior teammates are important
- What the ideal senior teammate looks like
- Healthy vs. unhealthy teams for promotion when it comes to seniority

After you find a more senior engineer to mentor you, follow the advice here: ["How do you get the most out of mentorship?"](https://www.jointaro.com/question/IbuZydz0QzsVVqESVaxQ/how-do-you-get-the-most-out-of-mentorship/)

Ace Your Tech Interview As A Software Engineer [Part 25] - Practical Coding

Practical interview coding rounds are the purest form of software engineering and what software engineers generally hope the interviews are (at least when they complain about data structures and algorithms problems online). This lesson teaches you:

- What a practical coding round is and when to expect it
- What kinds of companies give practical coding rounds
- How to prepare for practical coding rounds

To get the absolute best practice for practical coding rounds, check out our side projects playlist: [\[Taro Top 10\] Building Impressive Side Projects](https://www.jointaro.com/playlist/vKUWMgmmaEvzcYUXZs4B/)

MassMutual Case Study: The Ultimate Guide To Navigating A PIP

This was a new grad engineer who joined MassMutual, a 100+ year insurance company in Massachusetts.

- **Before**: First job out of college, shared a project with another new grad engineer which lacked support

- **During**: Shocked to receive it (did not know what a PIP was). Told not to ask for help to test his velocity

- **After**: Chose to leave the company, since the manager lost faith

Course Introduction: The Ultimate Guide To Navigating A Performance Improvement Plan (PIP)

You’ve probably heard about a PIP, a Performance Improvement Plan. You might be in danger of one, you’re going through one right now, or you’re about to join a company with a widespread PIP culture.

There’s no getting around it: **PIPs are scary.** Receiving a PIP means that there is a perceived deficiency in your performance, and something needs to change. It’s obvious why you might feel tremendous anxiety or fear around a PIP: your job is at stake.

Simply put, **a PIP is one of the most stressful things you can go through as a tech employee**. 

A quick online search reveals tons of discussion in forums about PIPs. It’s easy to get the impression that a PIP is a hopeless situation, and anyone who is unfortunate enough to receive one should simply give up. This is simply not true: whether you’re on a PIP or not, there is a path forward.

The objective for this course is to provide a structured way for you to identify what you can (and should) do to get the best outcome for yourself.

I’m Rahul, the course instructor. I’ve been an engineer at various-sized companies for a decade before I left to start Taro. I was an Engineering Manager and Staff Engineer at Meta (Facebook for the OGs), and before that I worked on Android at Pinterest. I graduated from Stanford with a Bachelor’s and Master’s degree in Computer Science, and my first job after graduation was founding engineer at a failed startup. 

In researching this course, I talked to dozens of engineers who have received PIPs, along with several managers who have delivered PIPs to their reports. You’ll hear some of their stories in the section dedicated to case studies (from companies like Amazon, Meta, Pinterest, MassMutual, and MongoDB). What became clear from chatting with so many employees is (1) there’s far too much stigma around a PIP and (2) there’s not enough support for people who have received one. This course aims to change that.

In addition, we’ve combined our own personal experience with dozens of hours of online research (we mostly ignored anonymous trolls in forums…).

I’ll occasionally refer to engineers throughout this course, but pretty much all the content is applicable to any type of tech worker (Product Manager, Data Scientist, Designer, etc). Software Engineers are not the only job function that must deal with a PIP!

Final note: my goal with this course it to be hyper-practical; this should be useful to you. I’ll be sharing best practices that have worked for many tech workers, but we can’t cover exact details across all companies in all geographies. I’m not an employment lawyer and I have never worked in Human Resources. You may want to get consultative help if your situation is unique. 

Connect with Rahul: 

- [Taro](https://www.jointaro.com/p/rahul-pandey/)
- [LinkedIn](https://www.linkedin.com/in/rpandey1234/)
- [YouTube](https://youtube.com/rpandey1234)

Read more about PIPs: 

- <https://jointaro.com/topic/performance-improvement-plan>
- <https://www.jointaro.com/blog/breaking-down-the-tech-company-mark-of-death-the-pip/>

The 4 Paths To Manager Growth. Choose One.

[**Ethan Evans**](https://www.linkedin.com/in/ethanevansvp/) is a retired Amazon VP who now teaches managers how to break into executive levels.

He shares how to get promoted as a front-line manager (M1). The pre-requisite is that you must do good work. This means motivating your team, delivering results, and organizing them effectively. M1s are focused inward and downward, with most of their time and attention on their team. M2s (managers of managers) focus on the bigger picture, considering how their team fits into the larger organization and collaborating for overall success.

**Four main ways to grow:**

- **Organic growth:** Your team and the company naturally expand, increasing your responsibility.
- **Filling holes:** Someone above you leaves, and you're chosen due to your performance.
- **Reorganizations:** Teams get shuffled, and you absorb parts of others' responsibilities.
- **Lead a new initiative:** Successfully launching a new project demonstrates leadership and initiative, potentially leading to promotion.

When times were good (i.e. metrics were strong and the company was doing well), there was more capacity for people to get promoted. For example, the gold, silver, and bronze medalist (3 people) may have gotten promoted, but in a stagnant company, only the gold medalist would get the promo.

Although you can't control when people leave or if there will be a re-org, what you can do is **focus on being the top performer:** Consistently deliver excellent results, demonstrate strong leadership, and be ready to take on additional responsibilities.

Relevant follow-ups:

- [Would you recommend SDEs try a rotation as an SDM?](https://www.jointaro.com/question/BRNUnPJ0y2BttQhPNmCu/would-you-recommend-sdes-try-a-rotation-as-an-sdm/?playlistId=oz0mnJvHHgM8NfVF7rgp)
- [\[Taro Top 10\] Software Engineer To Engineering Manager (IC -&gt; M Track)](https://www.jointaro.com/playlist/oz0mnJvHHgM8NfVF7rgp/)

Ask Me Anything (AMA) with a Disney Eng Director - Greg Benson

[**Greg Benson**](https://www.linkedin.com/in/greg7gkb/) is the Director of Engineering at Disney Streaming (Disney+, Hulu, ESPN+ Star+). Further questions and discussions are on the [AMA thread](https://www.jointaro.com/question/CdPjNOXvU882180yzs6R/im-greg-ex-googlenetflix-current-director-at-disney-ama/).

Previously, he was the Engineering Manager at Google, where he worked from 2017 - 2021. Prior to that, he was a manager at Netflix during the hypergrowth phase (2013 - 2017). Greg also has a deep background in music and audio, having received a Masters in Music & Audio Technology in 2003, and then working with Dolby for more than 5 years.

After leaving Google and before joining Disney, Greg took a career break to learn, explore, and recharge. He traveled to Ghana, learned about accounting, became a startup advisor, and read a lot.

Greg answered many questions in this Ask Me Anything (AMA). This session was moderated by [Igor Podkhodov](https://www.linkedin.com/in/podkhodov/). 

**Transitioning From Engineer to Manager: Insights and Expectations**

Greg shared his experience transitioning from an engineer to a management role. 

- Ask strategic questions in one-on-one and skip-level meetings, focusing on career trajectory and higher-level considerations. 
- Individual ownership and accountability are critical to ensure you succeed and build trust. 

They also discussed the purpose of skip-level meetings, which included understanding the expectations of senior staff and determining one's career trajectory. They emphasized the importance of adapting to different organizational and cultural contexts, as expectations can vary between companies. Igor added that it's important to verify the direction of one's actions during skip-level check-ins.

**Career Breaks and Influential Readings**

Greg discussed their influential reading materials, including [Creativity Inc](https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012), [Beyond Entrepreneurship](https://www.amazon.com/Beyond-Entrepreneurship-Turning-Business-Enduring/dp/0133815269), and [Leading Teams: Setting the Stage for Great Performances](https://www.amazon.com/Leading-Teams-Setting-Stage-Performances/dp/1578513332). He also shared their career journey, which involved tenures at Amazon, Netflix, and Google, a break of about a year and a half, and a transition to Disney. Greg quit his job at Google during the Covid-19 pandemic due to the challenges of remote work and the mental health burden. They emphasized the importance of taking breaks in one's career and the potential implications of extended gaps in one's employment history.

**Speeding up Engineering Velocity**

Greg discussed their experience at Disney, highlighting a less engineering-oriented approach compared to their previous roles. They also shared their insights on the factors that could accelerate an engineering team's velocity, such as testing, team culture, and the use of large systems. Greg further discussed the use of AI and large language models in the development process. During his time off, Greg learned more about AI and ML which helped him feel more confident in leveraging new advancements. For truly paradigm-shifting technologies (like AI), you won't be "too late" if you start adapting now.

**Mentorship and Career Growth**

Igor asked Greg about their approach to mentorship and its impact on their career growth. Greg shared that they have never used a career coach but has found mentorship through ad hoc interactions with colleagues. They emphasized the importance of reaching out to people for help and guidance, asserting that most people are willing to assist. They also shared their strategy of researching potential mentors before reaching out and being open-minded about learning from people in different roles and departments. Igor agreed with Greg's approach, noting the importance of persistence in finding a willing mentor.

**Career Progression**

- In a challenging economy (and world events), Greg advised holding out for a decent job that you're actually excited about, emphasizing the importance of following interests and passions. 
- Your specialization and expertise can help stand out in the job market. Startups often will have more growth and personal satisfaction. 

**Engineering Career Paths and Management Challenges**

Igor raised a question about career paths for engineers, emphasizing the need to understand motivations and challenges of growth into staff engineer or manager roles. Greg highlighted the significant responsibility that comes with a managerial role, including handling team issues, and advised finding an environment that supports career growth. They discussed the challenges and rewards of transitioning from an individual contributor to a managerial role, including loss of control, recognition, and specific deliverables, as well as the ambiguity and subjectivity of performance evaluation. The discussion ended open-ended with Prakash seeking insights on handling disagreements within teams.

**Managing Conflict: Strategies and Challenges**

Greg and Igor discussed the complexities of conflict within teams, with Greg sharing their experience and strategies for managing discord. Greg emphasized the importance of understanding power dynamics, providing coaching and feedback, and attempting to understand the other person's perspective. They also highlighted the challenges of balancing objectivity and support, and the importance of expressing empathy when disagreeing with someone. Igor shared their experience of trying to help a direct report dealing with personal issues, and learned the importance of empathy and understanding in communication. Greg also discussed the importance of different modes of listening, potential pitfalls of problem-solving over brainstorming, and the concept of escalation in conflict resolution. They suggested that if a manager is not supportive, it's important to know one's limits and consider finding a different team or having a direct conversation with the manager.

**Building Trust and Influence in the Workplace**

Greg shared his thoughts on building trust and influence in the workplace. 

- Honesty and transparency are paramount, with consistent actions over words. 
- Listening attentively and empathizing with others can help establish trust quickly. 

Greg also underscored the significance of documentation for accountability and avoiding circular conversations. They further discussed the involvement of politics in management roles, explaining that it's less about merit and more about relationships and perceptions. They clarified that healthy politics involves branding/reputation and accurately communicating achievements, rather than manipulating facts.

**Managing People and Avoiding Burnout**

Greg discussed their approach to managing people who don't read documentation, emphasizing the importance of empathy and support over shaming. They suggested providing opportunities for people to catch up, followed by a conversation if the issue persists. Igor then asked Greg about handling workload and avoiding burnout. Greg suggested contextualizing the effectiveness of meetings and encouraged individuals to assert agency over their time by choosing not to attend wasteful meetings, prioritizing their own work.

Further questions and discussions are on the [AMA thread](https://www.jointaro.com/question/CdPjNOXvU882180yzs6R/im-greg-ex-googlenetflix-current-director-at-disney-ama/).

Master The Art of Successful Negotiations: Unlock Your Full Potential

A practical negotiation workshop led by Nadav Klein, professor at INSEAD and instructor at Minerva Project. 

Nadav discussed the importance of negotiation skills in both professional and personal life, emphasizing the need to understand human behavior and the mechanics of negotiations. He highlighted the significance of practice -- the more you do it, the better you become!

It's important to identify zero-sum issues vs cooperative issues in negotiations. You should **strive to find ways to cooperate and create win-win situations by understanding and prioritizing the differences in what each party wants**. Critical to this is to bridge the information gaps and understand how we evaluate ourselves vs how others evaluate us.

- [Connect with Nadav on LinkedIn](https://www.linkedin.com/in/nadavklein/)

More resources on negotiations:
- [The #1 Rule Of Negotiation - How To Avoid Giving A Number](https://www.jointaro.com/lesson/4T3wTorG47wPzSqVmAOx/the-1-rule-of-negotiation-how-to-avoid-giving-a-number/)
- [[Case Study] How To Land 18 FAANG+ Offers With Steven Zhang (Airtable, USDR, Tableau)](https://www.jointaro.com/lesson/gGkO4pLeFq1ctRM9tSBF/case-study-how-to-land-18-faang-offers-with-steven-zhang-airtable-usdr-tableau/)
- [3 Quick, Powerful Negotiation Tips](https://www.jointaro.com/lesson/8VeEnbxdbPKsZbTcCFm5/3-quick-powerful-negotiation-tips/)

Does Your Job Performance Matter For Building A Startup?

In college, the common wisdom these days for Computer Science students is “your grades don’t matter, just focus on your network and building cool stuff.” 

**Does the same logic apply for aspiring entrepreneurs who are working in Big Tech?**

If you know you want to leave to start a startup, how much should you focus on getting the highest ratings and quickest promotions on the job, vs just doing enough to get by?

In Eric's case, he was was content with doing just enough to get by -- his time and energy was better spent preparing for his startup. Eric was barely getting a Meets All (MA) rating at Meta, and in fact, he was about to be put on a PIP before he left!

Instead of focusing on your ratings on the job, you should instead focus on having positive relationships with the people you work with. You want them to vouch for you as someone who is trustworthy, hard-working, and easy to work with. 

**Your network is your biggest asset as a founder.** Your job is not to be the expert who knows everything. Instead, your job is to have a deep network of people (advisors, friends, employees) who you can leverage to arrive at the best decision. 

---------
Connect with [Eric on LinkedIn](https://www.linkedin.com/in/ericbahn/)

[Part 7] Meta Intern Success Series - Succeeding As A Remote Intern

- Learning speed is severely nerfed by remote work, which is awful for you as an intern since this is when learning speed is the most important. It's important to keep this mind as you navigate your internship.
- Attend all team events, even the less formal ones (i.e. non-offsite) like team lunch. It's extremely important to build relationships and social capital in this environment where everyone is more isolated.
- Have 2 to 3 1:1s with your non-intern manager peers.
- Match the working hours of your team if you're in different time zones. It's absolutely vital that you always get blocked ASAP, and this is way harder when you're operating on a different time scale. This could be painful, but it will be worth it.
- Do virtual coworking whenever you can. The idea is that everyone joins a video call and just works, no meeting agenda or anything. The idea is to mimic an in-person working environment as much as possible. This creates peer pressure for you to be productive and makes it seamless for you to ask for help (just say something on the call!).

[Part 6] Meta Intern Success Series - How Most Interns Fail

Here are the common ways software engineer interns at Meta fail:
- **Misalignment of expectations**: Make sure that you're getting feedback regularly from your intern manager (IM) and ask every 2-3 weeks for a honest, real take on how you're trending. Don't wait until mid-cycle for real feedback!
- **Doesn't take feedback well**: Remember, feedback is a gift. Respond to it gracefully and quickly; treat every piece of feedback with urgency. As a software engineer intern, you barely know anything (which is expected): If you get constructive criticism, there is a 99% chance that it is correct.
- **Writes sloppy code**: Volume is straightforward and not that special - Most interns know how to write a lot of code from school. The point of your internship is mostly to teach you how to write good, clean, production-level code. Make sure your diffs are thoughtful, focused, and atomic with thorough context sections and test plans.
- **Sphere of influence is too small**: Don't only rely on your IM; you need to have 2-3 other peers to vouch for you in final calibrations. It can be comfortable asking your IM for help on everything, but you have to diversify: Make sure that you also ask other peers for help and to review your diffs. Consider having a recurring 1:1 (once every 3-4 weeks) with your non-IM peers.

[Part 4] Meta Intern Success Series - Working With Your Intern Manager

- Meet with your intern manager (IM) at least every week for 30+ minutes. Anything less is a recipe for failure as your software engineer internship is so short.
- Treat your IM as a resource, not a boss. They are there to help you. Don't be afraid to leverage them aggressively to unblock you.
- The incentives align between you and your IM. They get rewarded substantially if you get the return offer, and it's rough for them if you don't. It's in everyone's best interests for you to get more from your IM.
- **Do not hide issues**. If you have any sort of problem, whether it's a technical one or a mental/emotional one, share it with your IM. Learn to be vulnerable.
- Ask for feedback every 2-3 weeks, don't just wait for mid-cycle. You can ask how you're trending rating-wise to get a clear picture. It is hard to course correct if you come out of mid-cycle with a poor rating.
- Ask for feedback regularly and make it clear to your IM that you treat all feedback as a gift and you act on it fast (literally within a few hours/days).

Related resources:
- [You Should Be Vulnerable With Your Manager](https://link.jointaro.com/CCLPu9Pp6pmRrn427)
- [Having The Proper Mentality For Manager 1:1s](https://link.jointaro.com/wmxxUCrHKvUH1D4b8)
- [Suppress Your Instincts And Treat All Feedback As A Gift](https://link.jointaro.com/TsJKvMLrzvveMkpS9)
- [Full In-Depth 1 Hour Masterclass On Effective 1:1s](https://link.jointaro.com/67uVtoJWBYwrqgDJ7)

Real Stock Options Example - Kosei (Acquired By Pinterest)

This final segment offers a real-world walkthrough of a startup stock option offer and breaks down the critical information employees need to assess the *true* value of such equity. It highlights how confusing option grants can be without proper context and the financial implications of exercising options.

- **Real Offer Letter Example:** The speaker received an offer of 62,000 options at a $0.14 strike price, totaling $8,750 to exercise. However, the true value of this offer depends entirely on factors not included in the letter, like company valuation and total shares outstanding.
- **Vesting and Exercising Mechanics:** Vesting followed the standard schedule—1-year cliff with monthly vesting afterward. Post-termination, many startups only give a 90-day window to exercise, which can be financially burdensome.
- **Liquidity and Risk Considerations:** Employees may lose out if they can't afford to exercise before leaving a startup. As a response, some companies began extending the exercise window up to 10 years, reducing financial pressure on departing employees.
- **Tax Strategy Tip:** Exercising early (if financially feasible) starts the clock on long-term capital gains, which can save 10–12% in taxes versus short-term treatment if exercised and sold after a liquidity event.
- **Most Common Mistake:** Employees often overvalue large share numbers without understanding what fraction of the company those shares represent. To assess an offer, it’s essential to ask:
  - *What percentage of the company do these shares represent?*

  - *What is the current fair market value versus the strike price?*

Without those answers, it's impossible to accurately evaluate the worth of a stock option grant.

Tech Career Growth Videos

Our instructional videos provide software engineers with insights needed for career growth. Masterclasses go incredibly in-depth on a specific tech topic while case studies are real examples from established engineering leaders.