Career Development in Startups

I reviewed 100+ calls my team had with startups hiring engineers. Here's what they consistently care about right now, and what you can do to develop and show it. 1. Product-minded, with good taste Companies want people who care about what they're building and who have well-founded opinions about what "good" looks like. The best way to develop your product sense and taste is to build something you want for yourself, and then try to make it excellent by sweating the details. Generic side projects that anyone could have vibe-coded won't help you (in fact, they'll hurt you because they demonstrate bad taste). 2. Comfort with ambiguity and self-direction This was the next most consistently mentioned thing: Startups want people who can operate without detailed guidance. As one founder put it, "We need people who can figure things out on their own and don't need to be told what to do." You can show this with projects where you chose what to build, what to prioritize, and how to get unstuck. If you've only worked in big, bureaucratic environments, find opportunities outside of work to demonstrate your self-direction (or come do a batch of the Recurse Center). 3. Startup experience Startups look for people with past startup experience in part to filter out people who won't like working at a startup. As one hiring manager put it, "We really want people who know what they’re signing up for." If you've worked at a startup before, this is easy. If you haven't, be clear that you're comfortable with things changing quickly, working hard, and wearing many hats. 4. Pleasant and collaborative As one founder put it, "Being pleasant to work with matters a lot at a small company where you’re in the trenches together." We can all choose to be kind, flexible, positive, and humble in our lives and work. Doing so isn't easy, but it will make you a better colleague (and probably a happier person). Companies assume technical skills as a baseline; what sets you apart is your ability to thrive in unstructured environments while being a great teammate.

One of the best things about working at a startup? You really get to know your team—not just who they are today, but who they COULD become tomorrow. Startups evolve quickly. Roles shift. Needs change. And that creates an incredible opportunity for growth—for the company and the people building it. As a leader, one of the most valuable things you can do is recognize potential before a title or job description makes it obvious. When you start thinking about how someone’s strengths could shape the company’s future, not just fit today’s tasks, you unlock all kinds of possibilities for career growth and impact. Here are a few things I look for when thinking about how a team member might grow into a new or expanded role: • Curiosity and a willingness to learn new things • Initiative—do they step up when something needs doing, even if it’s not “their job”? • Pattern-spotting: do they notice things that others miss and ask smart questions? • Enthusiasm for helping others succeed (this often signals great leadership potential) • The ability to stay calm and solutions-oriented when things are messy (because, let’s be real, startups are often messy!) • A desire for impact—not just doing the work, but caring about why it matters • Awareness and understanding of how their work impacts the bigger picture • Cross-functional collaboration and empathy — but also knowing how to push things forward if they are blocked • Desire to dig into the data to find trends and patterns that can lead to insights that help move the business forward It's exciting to help shape careers in real time. Even more exciting? Watching someone grow into a role they didn’t even know they were ready for—until they were. What would you add?

𝗦𝗵𝗼𝘂𝗹𝗱 𝘆𝗼𝘂 𝘄𝗼𝗿𝗸 𝗳𝗼𝗿 𝗮 𝗦𝘁𝗮𝗿𝘁-𝘂𝗽 𝗼𝗿 𝘀𝗺𝗮𝗹𝗹𝗲𝗿 𝗰𝗼𝗺𝗽𝗮𝗻𝘆 𝗮𝘀 𝗮 𝗖𝗦𝗠? The startup CSM paradox: wearing eight different hats while earning less than your enterprise counterparts...here are the pros and cons. Here I am troubleshooting an inventory robot that malfunctioned in Japan. In true startup fashion, I was simultaneously handling sales, customer success, and support. ...as the saying goes..."go to your customers" 𝗣𝗿𝗼𝘀: 𝗛𝗶𝗿𝗶𝗻𝗴 𝗔𝗰𝗰𝗲𝘀𝘀: Easier to break in, connect with the C-suite and ask for the interview if you have a compelling message and hook. 𝗤𝘂𝗶𝗰𝗸𝗲𝗿 𝗣𝗿𝗼𝗺𝗼𝘁𝗶𝗼𝗻: As long as you are creating impact you can quickly move up in the company. 𝗕𝗿𝗼𝗮𝗱𝗲𝗿 𝗜𝗺𝗽𝗮𝗰𝘁: Your work directly influences company growth and direction. Every customer win feels meaningful and visible. 𝗩𝗲𝗿𝘀𝗮𝘁𝗶𝗹𝗶𝘁𝘆: You'll wear many hats beyond traditional CSM responsibilities—from product feedback, sales and almost always support. 𝗔𝗰𝗰𝗲𝗹𝗲𝗿𝗮𝘁𝗲𝗱 𝗚𝗿𝗼𝘄𝘁𝗵: Rapid learning environment where you develop skills across multiple domains simultaneously. 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆: Your contributions are noticed, making it easier to demonstrate your value and impact. 𝗔𝘂𝘁𝗼𝗻𝗼𝗺𝘆: Typically less bureaucracy means you can implement innovative solutions without navigating complex approval processes. 𝗘𝗾𝘂𝗶𝘁𝘆: If it's successful you can cash in that lottery ticket of equity. 𝗖𝗼𝗻𝘀: 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲 𝗟𝗶𝗺𝗶𝘁𝗮𝘁𝗶𝗼𝗻𝘀: Often working with smaller teams and tighter budgets, requiring creative problem-solving when resources are stretched. 𝗣𝗿𝗼𝗰𝗲𝘀𝘀 𝗗𝗲𝘃𝗲𝗹𝗼𝗽𝗺𝗲𝗻𝘁: You may need to build customer success frameworks from scratch rather than following established systems. 𝗪𝗼𝗿𝗸-𝗟𝗶𝗳𝗲 𝗕𝗮𝗹𝗮𝗻𝗰𝗲: The "all hands on deck" nature can lead to longer hours and blurred boundaries between work and personal time. 𝗖𝗼𝗺𝗽𝗲𝗻𝘀𝗮𝘁𝗶𝗼𝗻 𝗦𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲: While equity opportunities exist, base compensation and benefits packages may be less competitive than at larger companies. 𝗧𝗼𝗼𝗹 𝗖𝗼𝗻𝘀𝘁𝗿𝗮𝗶𝗻𝘁𝘀: You might work with simpler tech stacks or need to justify investments in customer success tools. 𝗖𝗮𝗿𝗲𝗲𝗿 𝗣𝗮𝘁𝗵 𝗨𝗻𝗰𝗲𝗿𝘁𝗮𝗶𝗻𝘁𝘆: Less defined advancement tracks compared to larger organizations with established CS hierarchies. For those who thrive in dynamic environments and value impact over structure, startup CS roles can be incredibly rewarding. But they require adaptability, resilience, and comfort with ambiguity. What has been your experience? Are there other pros/cons?  #CustomerSuccess #Startups #CareerAdvice #SaaS

Big companies have the brand names, but small companies have unique advantages in attracting top talent. Here's how they can win: Speed & Decision Making: • One conversation vs. five committees • Offer letters in days, not weeks • Custom roles built for great candidates • Flexible compensation structures Real Impact & Growth: • Direct access to leadership • Immediate visible impact • Broad experience vs. narrow focus • Build something from the ground up • True ownership in outcomes Career Development: • Rapid advancement opportunities • Learn multiple aspects of the business • Direct mentorship from leaders • Create your own path Identify what matters most to each candidate. For some, it's faster growth. For others, it's broader experience or direct impact. Small companies can't compete on brand name - but they can offer something potentially more valuable: the chance to truly shape both the company and your career.

If I was desperate for a job, I wouldn’t waste time applying on job portals. Instead, I’d focus on positioning myself where there’s less competition and a real eagerness to hire. Where’s that? Freshly funded startups. Here’s my step-by-step plan, and why it works: Why It Works: Startups move fast – They don’t have the luxury of drawn-out hiring processes. [A] They need talent now – Many freshly funded startups have urgent hiring needs as they try to scale quickly after receiving investment. [b] Less competition – Fewer people apply directly to startups, especially if you catch them early. [3] Flexible for hustlers - Many startups are hiring for multiple roles, and they’re more open to taking chances on people who can help them grow fast. It’s a much better strategy than waiting for a response in your inbox! [1] Find Freshly Funded Startups Check out media sources like YourStory's weekly funding reports, TechCrunch, or Crunchbase. These startups have just received funding and are often eager to grow their teams quickly. [2] Do Your Research Take time to understand the industry the startup is in, the problems they’re trying to solve, and where they’re headed. This way, you can position yourself as someone who “gets” what they’re about. [3] Create Your Unique Selling Point (USP) Based on your research, figure out how your skills fit into their growth. Make your pitch tailored to their specific needs, so they see you as someone who can add immediate value. [4] Network on LinkedIn Start connecting with key people at the startup, such as recruiters, hiring managers, and team leads. Personalize your connection requests, mentioning why you’re interested in their company. [5] Pitch Yourself Once you've made those connections and done your research, pitch yourself directly. Explain why you're excited about the company, how your skills can help them solve specific challenges, and why you're a great fit for their current phase of growth. Do this if you are are struggling to get a job!

Starting your career at a startup can be a massive career accelerator. Problem is, starting it at the wrong one can be a career hindrance. Of course, I'm not saying you need to pick a future billion dollar company when they are just starting out. Not even the best investors in the world can do that 100% of the time. But many of the best startups have similar characteristics, and even if they don't become that unicorn you are hoping for, they can still be a great starting point for your career. So, how should you choose? Here's how I think about it: 1. Talent brand — are the people at the company exceptional? If so, even if the startup doesn't work out, that network and brand will still be valuable. 2. Strong leadership — are the leaders at the company people you trust? Are they deeply committed? Do they have a pattern of success in their career? Are they people you are excited to learn from? Btw, just because they have a fancy company on their resume does not mean this box is checked. 3. Stage — pre-revenue, pre-PMF, and post-PMF companies are all very different. Be mindful of the trade-offs and take stage risk when you are passionate about the product and the team is exceptional. 4. Intensity & pace — does the company move quickly, not just for speed's sake, but because they know that is the best way for them to be successful? Btw, that doesn't mean they have to work 24/7 (although some startups do), but they should move with urgency and have a healthy paranoia. 5. Team size & ownership — companies with <30 employees are more chaotic, but that also means there's more opportunity to have an outsized impact and thus end up with outsized ownership. 6. Financial health — is the company well-funded or are employees being paid in IOUs? Of course, raising venture capital does not solve all problems, but you don't want to be stressed that the company is always about to die. Historically, when college students would reach out to me about finding great companies to start their career at, I would always refer them to the Breakout List and Wealthfront's Top Companies List. Unfortunately, both went away in the past few years. Glad to see Tyler launch his new "Exceptional Startups List" today: https://lnkd.in/gMc_PWDc Check it out. Would imagine many of these companies are hiring. #startups

Last week, someone asked me this question re: #startups. Sharing my advice below! Q: What is your perspective on taking quite big step downs in pay / responsibility, in order to join these size/stage firms? My advice: 1/ It depends on your career goal > Is joining a startup the best next step in order to reach your ultimate ambition? > (Perhaps, yes, if you want to run an SME or start your own business). 2/ Be clear what you mean by "startup" > In my experience, people use this term to refer to anything from a 1 person business to a series E+ international business with 1,000+ FTE (and everything in between). > Each stage has different challenges, different job opportunities etc. Which are you focused on & why? 3/ Pay depends on stage > On average (based on my data), startup salaries are ~20% below market. This narrows as the company gets bigger. > Interestingly, startup employees report well above average satisfaction with their pay. Perhaps explained by a closer connection with mission / impact via being in a smaller team. What's most important to you? If it's purely the year 1 total cash comp, startups (of any scale) are unlikely to be the best place. 4/ The makeup of pay is different vs corporates > Most important to appreciate is that packages are typically more simple than in corporates. Bonuses are rare (often these are loss making businesses). Benefits are less developed. Typically it's basic salary + options (often depending on seniority). > And remember, options are worthless until there's an exit event - so stress test your confidence in that happening, if you're banking on that value crystalizing to make the career move stack up. 5/ Responsibility can actually be far greater. It depends how you define it / what responsibility you value > If you're referring purely to team size, you might manage fewer people > But your decision making power may well be far greater than in a more complex organisation. Less bureaucracy. And fewer safety nets. 👉 Joined a startup? > Does my advice resonate? > What would you add? - - - ps. Over the past month or so, I've recorded my advice on 100+ career FAQs like this - all sent to me by people in my network! 📌 You can check out some of the videos for free here: https://lnkd.in/ekkNXxmu

PSA for anyone early in their career considering joining a start up… 🔑 If your primary motivation to join is comp or upside from equity, you will most likely be disappointed. 🛑 I have spent my whole career in start ups and have been lucky enough to reap the rewards of early stage equity. 💰 But I know it’s rare and typically not life changing money unless you are the founder. ✔️ The best reasons to go to an early stage company with much higher risk is to get a chance… 1️⃣ at doing stuff you wouldn’t be allowed to do at a later stage company. It’s the best place to learn by doing. No / minimal swim lanes or political BS to navigate. 2️⃣ to accelerate your career early on. If you get sh*# done regardless of your ‘level’ - you will be recognized for it with more responsibility faster than you would at a company with defined career tracks 3️⃣ to work directly with senior folks (founders, exec team) that are smart, resourceful and experienced vs working with folks with similar experience as you in a large company If you like being self directed and *learn primarily by doing*, startups may be the right answer for you. 💪 But if you prefer to have *defined playbooks and learn in a structured setting*, large companies may be your best bet.🙌 No wrong choice. But each choice has a trade off 😊 pick wisely! Run your own race 🏃♀️ #startups #careermanagement #earlyemployees #careerinsights

A couple weeks ago, I shared a story about the scrappy beginnings of Energy Terminal and how we landed interviews with CEOs of billion-dollar companies while recording podcasts on a stack of library books. Core message: starting something will accelerate your learning curve 10-X. However, even if it's not you starting the company, joining a startup can deliver a lot of the same benefits. Here are a few reasons why startups can offer significantly-differentiated learning opportunities, especially early in your career: --> Ownership and Impact: At a startup, your work has real, tangible consequences. You’re not in the machine--you're building the machine. It’s a place where you can punch way beyond your weight, contributing to big wins and solving big problems in ways you might not get to at a larger company. You'll probably be doing things your peers at big companies won't get to do for a decade. -->Speed and Agility: Startups move fast. Decisions that might take months elsewhere are made in minutes. The pace can be intense, but it teaches you how to execute quickly and effectively, with no time to overthink or second-guess. -->Multi-Disciplinary Learning: Startups are the ultimate crash course in learning by doing. One day you’re refining a pitch deck for investors, and the next, you’re troubleshooting technical details with engineers. The breadth of experience you gain is unmatched, and it’s this variety that accelerates personal and professional growth. Joining a startup isn’t easy. It can be messy, fast-paced, and uncertain. But the payoff? You'll have the opportunity to accelerate your career growth far faster. Photo: Representing DG Matrix at an industry conference...probably something I wouldn't have gotten to do at a larger company! #startup #entrepreneurship

Here’s an objective and analytical comparison of working in a startup vs. an MNC for a fresher, focusing on key factors: 1. #LearningOpportunities   - #Startups: Freshers often get exposure to various roles and responsibilities across departments due to smaller teams. This leads to faster hands-on learning, problem-solving, and a deeper understanding of the business. Freshers might need to wear multiple hats and learn new skills quickly.   - #MNC: Training is more structured, with specific job roles and responsibilities. Learning is more incremental but steady, focused on the particular area assigned to the fresher. MNCs often provide access to formal mentorship, extensive resources, and long-term career development programs. 2. #JobSecurity   - Startup: Higher risk especially in early-stage startups. However, in case of growth, there could be greater personal rewards (e.g., equity, recognition).   - MNC: More stable environment with greater job security. However, the chances of quick progression or impactful contribution may be lower. 3. #WorkCulture   - Startup: A more dynamic, fast-paced environment with less bureaucracy. Decision-making is quicker, and freshers may have more influence over business decisions. Work-life balance may be compromised due to longer hours.   - MNC: More formal, hierarchical structure. Work-life balance is generally better due to defined work hours and processes. However, decision-making can be slower, and freshers may feel less involved in larger strategic decisions. 4. #Growth   - Startup: Potential for rapid career growth. Freshers can often take on leadership roles faster as the company scales.   - MNC: Career growth follows a more traditional path with clear metrics and timelines for promotions. Growth is often slower. 5. #Salary & #Benefits   - Startup: Salaries may be same or slighty lower initially, but startups often offer equity or stock options as part of compensation. Good increments.    - MNC: Generally offers better pay packages—industry average increments. 6. #Innovation & Exposure   - Startup: Freshers in startups are exposed to cutting-edge technologies or innovative business models. There’s more flexibility to experiment with new ideas, leading to potential breakthroughs.   - MNC: While MNCs do innovate, the scope of innovation can be more controlled and process-driven. Freshers may work on large-scale projects, but innovation often occurs within established frameworks. Conclusion: - Startups are best for freshers who are adaptable, willing to take risks, and interested in a fast-paced, all-encompassing learning environment with potential for high reward. - MNCs suit freshers who seek stability, structured growth, and a defined career path within a specific field of expertise. Your decision would depend on your risk tolerance, career goals, and learning preferences. #NoOneSizeFitsAll Do add in if I have missed anything.