🔖 The Generalist’s Job Search in 2023

👋 Welcome to this Q&A article by GW member, Lorel Sim. Lorel spoke with Tak Nguyen, Founder and Managing Partner at Plenty Search. A huge thank you to Tak for sharing his insights with the Generalist World community.

As generalists in the tech industry, we find ourselves in a unique yet challenging period. On one hand, there are significant functional and domain-specific opportunities emerging, as more talent identifies themselves as generalists and we witness remarkable progress in AI, digital health, and climate tech. On the other hand, companies of all sizes are resorting to layoffs and reorganizations to extend their runway by an additional 18-24 months to stay afloat until venture capitalists are ready to fund again.

To help you navigate the current job market and leverage your generalist potential, we interviewed Tak Nguyen, Founder and Managing Partner at Plenty Search. Tak discovered his passion early on for transforming people's lives by connecting them to meaningful careers. He has worked with large corporations such as Disney and Google, as well as fast-growing startups like Airbnb, Care/Of, and Sword Health.

Our Q&A delves into both the job market's and job seeker's perspectives.

🗺️ Understand How Companies Build Hiring Roadmaps

As Tak shares, hiring is never an exact science, and scaling companies are learning, growing, and making their own mistakes. It’s important for candidates to understand what’s happening on the other side of the table in order to properly assess their opportunities and the health of the companies they’re applying to. If you’re a job seeker, you should treat your interviews as a two-way street - an opportunity to ask about near-term growth plans and hiring roadmaps. Here’s a little more context on how companies are thinking.

Q: What does a startup team need to consider while building its hiring roadmap?

A: If I were to offer one general principle for early-stage companies, it is actually to resist the temptation to hire too fast. There’s a bit of a bias that headcount growth directly relates to revenue growth, and startups wear that as a badge of honor. We actually fell into that trap at Airbnb before auditing the process and getting more disciplined. But there was a lot of wasted inefficiency before we got there. One company that I believe has modeled this incredibly well is Netflix - they believe in talent density. This isn’t just because of cost, but because people do better work when everyone has a reason for being in the room and there isn’t unnecessary bureaucracy. And for talent, we have a responsibility to hire thoughtfully in order to eliminate the level of churn that we are seeing today.

Q: Is there a methodology that leadership teams can use to hire intelligently?

There are 3 steps that come before making a full-time (FT) hire.

1. Instead of immediately jumping to saying, “we need a FT hire,” think about whether there’s a way to change processes and systems to boost efficiency.

2. Ask your teams if there are tools or technology that can automate the work.

3. Ask whether this is a long-term need or a temporary need. If it’s temporary, think about finding a great contractor to bridge the gaps.

4. And lastly, if none of these options work, add a full-time hire.

Q: What’s the biggest shift you’ve seen in the general Talent function’s philosophy over the past decade?

A: This is a really positive one - there is much more awareness of and focus on DEI. 10 years ago, if you mentioned DEI, people wouldn’t understand the term and so we couldn’t have a conversation. To be clear, there’s still a lot of work to be done, but we should consider it a win that we have set the stage for companies and recruiting teams to have meaningful conversations about representation and biases.

🎯 Positioning Yourself in the Job-Seeking Process

For generalists in the job market, it’s important to benchmark job titles, understand the types of companies that you’ll thrive in, and properly frame transferable skills.

Q: As companies tighten up their workforces, what advice can you give to candidates?

A: I’ll segment this further into two questions: What’s the right job? And how do you market yourself for it? Just because you know that a job is a good fit for you doesn’t mean it’s obvious to the market.

Titles are weird. There isn’t a lot of uniformity across companies. For example, Salesforce is known to be very title-inflating, while Apple is known to be quite title-deflating. A Salesforce VP might have the same scope as a Manager at Apple. So all companies are different, and you need to know what the titles on your resume mean to the market and whether they correlate with your search. If you were a Director of Business Operations, but your scope changed as they do in startup world and you actually spent more time managing Customer Success, ask your manager if you can adjust the title to match your experience.

Q: Knowing what you know about our generalist community, where do you think they’d thrive?

A: I’m definitely thinking an earlier stage company. Generalists may be frustrated at larger companies where a Product Manager manages a very small feature in one suite. That’s excellent for specialists who want to build in one area, but as a generalist you’ll feel like your scope is limited. At startups with 10-25 employees, there is plenty of work that is loosely defined, giving generalists opportunities to explore their interests and strengths. Even startups have highly defined engineering, marketing, and product teams, but the area in-between of strategy, operations, legal, HR, and finance is where generalists can add value.If you're a generalist looking to become a CEO or entrepreneur someday, startups are great places to learn how to run a business. And even within those functions that are more loosely defined at startups, reflect on what has brought you the most joy. Was it working on the pitch deck for the fundraise, or was it figuring out the budget? Lean into that.

Q: What do you like to hear in response to “tell me about yourself?”

A: Rather than a soliloquy, I strongly prefer a 2-3 minute overview of a candidate's experience and achievements across different roles. Candidates should also incorporate their narrative and why they decided to pursue certain jobs. For example, "I moved into this role because I'm passionate about building teams and wanted to work with people" or "I love working with customers and have a lot of empathy for them, which is why I became a customer success manager."

Q: Awesome - and lastly, which industries is Plenty Search excited about in the coming years?

A: Generative AI at the intersection of other industries, of course. And I still think we’re in chapter 1 of digital healthcare. We saw point solutions and low-level digitization come through, and now we’re already seeing deep technology clients enter the market. And this is where our top candidates want to be. Millennials and Gen Z care about purpose-driven work, and there’s no greater purpose than helping people live happier, healthier lives.

Meet the author: Lorel is a serial startup generalist (read: GTM, Product, BizOps) and has spent the past several years growing consumer brands and digital health businesses. She loves working on projects that bring immediate value to the everyday consumer, and is always on the lookout for the best new products and tools in wellness. West Coast born and raised, she now lives in Miami. Connect with Lorel on Twitter or LinkedIn.