AMA on Growing Your Career in Content with Maggie Leung

Welcome to our AMA with Maggie Leung, VP of Content at ClickUp and ex-NerdWallet VP of content and a16z executive editor.

Maggie Leung has spent nine years in content (building NerdWallet’s content team and operations from scratch + exec editor at Andreessen Horowitz + now VP of content and organic growth at ClickUp) and decades in news (CNN, the Washington Post, the Wall Street Journal and other newspapers).

This AMA (orginally held in the Superpath Slack) covers:

• Career development & leadership
• Navigating transitions
• Interviewing & hiring with confidence
• ...and more!

You can connect with Maggie on LinkedIn.

You are very good at transitions, whether it's moving from a contributor role to a management one; or from one company to another. How do you know when it's time to transition in your career? How do evaluate what transitions are worth making?

Maggie: I don’t think there’s a standard answer. For me, I always try to keep learning and leaning into discomfort. If I’m getting comfortable, that’s my signal

What advice do you have for someone looking to transition from a very small company to a larger company with bigger clients, more talent, and more career development opportunities? How does that person break out of the super small space and demonstrate that they are capable? What do you look for when hiring less experienced candidates?

Maggie: Whatever you’re aiming for, do homework on your targets. Like I can check on LinkedIn and elsewhere and tell you how a company hires based on who’s on their team.

If I saw them hiring traditionally — lots of degrees, credentials, seasoned people, etc. — I am not gonna waste my time pursuing them vs. companies with different profiles. Many smaller companies and agencies have team bio pages. You can check there as well.

How I evaluate opportunities: I layer my life priorities and personality over the opportunities.

Don’t get distracted by shiny objects. Always know what you want next, even if it’s vague. Like I knew I wanted to try B2B SaaS more than two years ago, while still happy at NerdWallet. I started reading up, etc. to prime myself.

I had lots of recruiting inbound meanwhile but I always benchmarked them against what I wanted. If they turned out to be more compelling, at least I’d know what I was trading off.

People often get distracted by what’s easy or what comes their way.

It’s fine to change course, but I prefer to do it mindfully.

What was it like to manage 100 writers/editors at NerdWallet? Any tips for people who want to get better at people management?

Maggie: First three years were the hardest because your startup has no recruiting juice and might be a pop up tent for all people know. You have to prove yourself before you can get lots of proven talent. And if you hire too many compromise candidates, especially managers, you’ll create a low ceiling for your team. You have to keep that in mind while building. Like I didn’t sacrifice and hire weak mgrs just to lower my workload early on. It took 14 months of intense building just to prove to great mgrs that we were worth joining.

If you want to become a great mgr, work where you have role models or anti role models and observe closely. For every screwed up mgr I saw in newsrooms while in journalism, I learned what not to do.

When you see people struggle or fail, break it down mentally — why, what could they have done differently, etc.

Look for takeaways in all instances and you’ll build mental models.

NerdWallet has become kind of famous for its SEO dominance. Can you share insights into building that team, working with SEO folks, technical challenges or anything else about that experience?

Maggie: No. 1: I never believed in isolating SEO expertise in a center of excellence. Long before we hired SEO experts at NerdWallet, we taught every single content person SEO and kept upgrading their skills, sharing learnings and experiments.

Why: say you have chefs. They understand food, techniques, cuisines, food chemistry, ingredients, etc. That means they can create recipes.

Or you have cooks, who follow others’ recipes. Who do you think will make better food? Who will be more likely to win Michelin stars?

That’s how I thought about SEO at NerdWallet.

And the more chefs you have, the harder it will be for competitors to take you down.

That includes hiring away any individuals and leaving you with single points of failure.

Every NerdWallet content person is better skilled than many of their peers outside. We invested in them with the long term goal of becoming a trusted household brand across generations.

Not every company shoots for long term. I was very clear on what we were aiming at and the earning horizon that would require.

What has your experience been like with mentorship? Have you had mentors and how did you find them? And what do you look for in a mentee?

Maggie: I don’t count on having mentors because that’s usually not in your control. When I have developed valuable mentor relationships I’ve never asked them to mentor me — we kept talking and clicking and it became a longer thing. Great mentors are asked more than they can handle. Show them why you’re worth investing in. Don’t waste time asking sh-t you can Google or learn easily. Figure out the key things they can help with. Like I’ll learn something and ask for 20 mins time and ask smart enough Qs that they’ll give me more time later. And so on.

I mentor folks who I think are good investments — they’re likely to integrate info and apply, and they’re likely to teach others. I look for compound growth.

I’d love to hear your opinion on generative AI and the future of content marketing / content marketing careers. I’ve heard lots of different tales but I’m curious about your perspective given your position and experience working with content teams at scale.

Maggie: AI will eat the lunch of people who do low end work.

People who leverage AI for low end work and add human value — connecting dots, coming up with strategy, layering and connecting disparate topics or SME — will benefit from AI.

Many businesses will benefit from AI.

The bar will be raised overall on content, but there will be a lot more noise to signal.

I was reading through your LI profile and one thing that stood out is your approach to building a bench nonstop, as well as succession planning. I’d love to hear more about how you’ve approached this with teams of different sizes—what are a few things every leader should be doing or temp checking regularly? How do you think about zooming out to see the longer horizon?

Maggie: Always start with the business and its goals. That’s because cookie cutting ways of building can be totally off and needlessly expensive.

You have to consider the business, goals (short, midterm and long), its runway, its competitors and space.

Like I do not recommend our approach on NerdWallet Content as a uniform approach. I happened to lean toward companies that think longer term, so it matches what I like to build best. If I had to, I could build a sweatshop with no bench. But I hope I never have to.

Staging also is important. Like an early stage startup shouldn’t spend too much time thinking too long term. It’s ok directionally, but if you overweight on long term and don’t see what’s really in front of you that needs doing, you could have no business to run midterm haha.

Wondering if you have any book (or other resource) recommendations around leading a content team? Not only the "soft side" of people leadership, but also how to structure and run the function.

Maggie: I’m sure other folks can recommend resources better than I can.

I learn a lot by observing, reading online — I Google a f--k ton — and can’t even remember where I learned what I also spend a lot of time thinking thru, like game theory — hypothesis, potential outcomes, best and worst case, what the ripples and downstream effects might look like. I’ve gotten better at that over years. When I joined NerdWallet from mainstream news, I didn’t know SEO, funnels, etc. I didn’t even know what a CTA was.

I compare content and thought leadership. Very little is directly applicable because each business is different.  Even in the same kind of businesses, you can’t cookie cutter and hope to outcompete.

Maybe useful: These 13 Exercises Will Prepare You for Work's Toughest Situations

This is like five years old I think. That’s soft skills. With orgs, I don’t believe in standardized org structure. Build what your company needs and keep reorganizing as needed as it (hopefully) grows.

We reorganized our content team at NerdWallet multiple times as business needs evolved. It’s never going to stop if your business thrives.

I also follow thought leaders in many spaces. They all have useful stuff you can apply, rework to fit your needs. The best in their field are often the sharpest thinkers about how to build and grow.

Can you talk about the skills you marketed and honed as you moved from newsroom to building content for companies outside of traditional journalism. I've been trying to figure out how make the switch, and would appreciate any tactical advice you can offer here.

Maggie: Shift mindset. Understand what your role really is in a new industry, business, company, team.

Many traditional journalists (not all of course) see themselves as speaking truth to power, holding people and companies accountable, etc.

That is not at all your role in most other companies. Sounds easy but many journalists fail at this when transitioning.

If you join a business, you’re signing up to help solve all its problems, leverage its opportunities, to be part of the team, on the side of the business. You are not there to critique or hold people accountable. If you try that, people probably will hate your guts and you’ll be essentially worth little.

Learn the business as much as possible — learn business model, users, competitors, etc.

Only then can you come up with worthwhile strategy that’s sustainably valuable. Sure you can throw sh-t against the wall a bit, but many people just lean into what they know or throw sh-t wildly.

Your a-- will be fired sooner than later if so. Or someone smarter will come along and add greater value.

One of the other key things about changing careers: don’t assume what was valued in your old career is valued in your new one. Like urgency was a priority in news. That’s not necessarily so in many businesses. They might for instance value stakeholder input, building or protecting brand more, etc.

Many people don’t know to unlearn sh-t as well as learn anew.

I've got a salary / earning potential question. Say you've got 2 years and you can only do 3 things to increase your salary 50-100%. What are those three things?

Maggie: Step back and look at where supply is much more limited than demand and is likely to continue that way.

Look at what’s complex vs. not.

Look at what’s boring or hard for others.

Look for industries or subject matter that requires explaining in detail.

If you do those things, you’ll see where there’s going to be a high barrier to entry or to competition and where building expertise will make you increasingly valuable.

Btw anyone who knows how to build strong content teams and groks business is already rare

When you’re being recruited for a role, what are the most illuminating questions you ask the recruiter/manager that help you evaluate the role, team, company, and opportunity?

Maggie: My first test is (in my mind): would I want this company to succeed even if I had nothing to do with it? If not, why would I ever consider working there? That’s from a position of privilege — many people don’t have that. Like I would’ve wanted NerdWallet to exist and win even had I never worked there, because it does good that I believe in.

No. 2: I look at the business fundamentals. If those aren’t sound, I’ll avoid. Why: if you assume you’re going to work hard, etc., why work at a place that’s probably gonna not do well or fail? You can’t do it all by yourself.

Then you look at leadership. Then whether they understand the value of content. I don’t work where I have to sell content uphill. You’ll waste your energy on convincing them to give you resources. How will you prove sh-t works then? It will be excruciatingly slow and wear you down.

How did you measure/track attribution at Nerd Wallet? (Not exactly career related I know, but probably helped with job security/leveling up)

Maggie: We started with Google analytics at early stage and eventually got more sophisticated over time. We did end up with multitouch attribution but didn’t rely on that for SEO.

Looking back to the early years of your career, what’s one thing you think you did that continues to pay dividends today? Also, what would you say are the top 5 qualities of the best talents you’ve managed?

Maggie: In my 20s I pursued a job overseas and got it, ended up miserable. I stepped back to break down why I’d ended up that way and realized I was rigid and narrow minded. And that I’d learned more in my significant discomfort than at any other point in life.

That changed how I look at discomfort and risks across the decades since. I’ve kept leaning into increasingly hard things and discomfort and that’s helped me build grit and guts.

And by taking risks and even falling short, you build mental models, judgment and confidence. Plus you realize what you’re made of and you realize plenty of sh-t doesn’t kill you, so you’re more willing to be brave.

I also have increasingly looked at things as experiments — keep emotional distance and see what the results are. Learn and be honest about what you screwed up. That way you’ll learn faster and no one can call you out on sh-t if you called yourself out first.

Top qualities:

• Don’t think in a box when it comes to their job.
• Have good judgment. Not perfect. But if I ask why you did something or approached it X way, I can follow your logic.
• Takes initiative.
• Takes feedback well. Not roll over and ingest everything like a dolt. Really consider what’s true and useful and apply itIs introspective. If you’re not, you’ll miss a lot of learning in life and work. And as a manager, I can’t follow anyone around and be telling them all of X. Most of the time, your manager isn’t even around.

I am hiring for a writer and have found it incredibly hard to get candidates with samples up to our standards. Where do you draw the line on the bar for existing talent vs what you can train for on the job? And what has been most effective for you in conducting that training to level up your team?

Maggie: Hiring depends on 1. What resources you have. 2. How long you can afford to look.

If No. 1 is weak, you should have realistic expectations. You might have to settle more than you’d like. And train as you’re able.

Alternatively, you could go into the wild and look for people whose work you think is strong and recruit them or at least learn what they’d cost if they were available. That can help you check or adjust your expectations.

Or even if they’re not available, maybe they can refer people who are as good — people usually recognize talent similar to theirs and have such folks in their network. This works only if you can afford them.

When I hire, I always test finalists for staff roles. If their test story is within 80 percent of what we need, then we give them feedback and see how they improve the story. If they can’t do that well and/or aren’t receptive to feedback, move on — you don’t want to hire yourself a problem.

Anyone under 80 percent (based on experience level, because you can’t use the same yardstick across the board), I pass on. It’s not that they can’t learn. It’s that they probably can’t close the gap at business speed and/or we won’t get strong enough ROI from training them. If you think they’re promising, you can always encourage them to apply again after they’ve gained more experience elsewhere.

For all roles, I think agnostically. Like imagine two writers each make $100k at market rate. Say one produces turnkey work vs. the other does work that needs a lot of editing. If so, then I’m overpaying the second one.

Of course, very few writers consistently file turnkey copy. The point is, I factor all training, editing, managing into the cost of anyone I hire and manage. If they’re consuming too much of any of those elements vs. their peers (with relative experience level), why would they be a good investment? The only way that makes sense is if I think they’ll outperform by a significant margin after training. Or I discount their pay enough to cover all the extra costs of what they’re consuming.

Note: Managers should do this sort of mental math, because companies pay us to be good stewards of resources, among other things. If you don’t, then you’re likely giving competitors an advantage. Companies hire people like me to see that we compete strongly. I always remember that. Plus, if you receive equity, you should be extra incentivized to remember that — you co-own part of the business, so don’t burn resources unnecessarily.

About what’s effective for training, I build teams at scale, so your answer might vary:

In your case, you might be the one doing all the editing, coaching and training.

In my case, I hire strong editors and I expect them to up-level writers so they need less and less editing and managing over time.

I don’t want editors who just keep fixing the same problems and the writers don’t progress. That would be bad for the company, team and writer, because how are they ever supposed to get stronger and earn more? (This assumes you’re not running a sweatshop, which is a privilege not everyone has. And I don’t judge even if you have to run one — not everyone gets great opportunities and sometimes you have to take steppingstone roles and work your way up.)

Depending on your team, I’d also suggest leveraging existing talent to help uplevel teammates. Like at NerdWallet, we’d hire people with varying experience levels. If you were a seasoned writer or editor / manager, we automatically expected you to help less experienced peers via mentoring, coaching, peer editing or such. That included doing brown bag lunches (we did that virtually, because our team was remote), etc.

We screened for such characteristics when hiring. That also was part of how we evaluated people, part of how we determined raises and promotions. It was embedded across our team culture and you’d see it happening all around you.

If you didn’t do this, we’d coach you to and keep pressing for it. We had an instance where a highly skilled X kept backsliding and just wanted to mind their own knitting, instead of being a good teammate. We ended up laying them off.

I mention that, because if you value something as a team, you have to protect it against people who don’t live those values. They’re not necessarily ill intentioned, but they erode your values. Other folks will see they’re not doing X and getting away with it. That signals that you think that’s OK. And you’ll demoralize them, because are they chumps for doing X while someone else doesn’t?

With a strong, collaborative learning culture, not only do you get better results from pooling know-how, people learn additional skills — they learn to teach, coach and mentor. That makes them more marketable. They can carry that with them well beyond one job and potentially earn more.

Almost always, anyone who worked on NerdWallet Content ended up being significantly more marketable than when they joined us. Other companies frequently tried to poach from our team. (This adds to your recruiting juice, of course.)

Sure, you give people raises as they gain valuable skills, but those are just table stakes. Top talent can make money at various places. Among many companies in tech, it’s also not unusual to get equity, good benefits and perks.

It was part of our job as managers to make sure that we gave people more reasons to stay. That included the sense of being seen and valued as an individual, meaningful work that was connected to our mission, career growth, autonomy and flexibility, great managers and terrific teammates who cared about them, etc.

If you can’t provide those sorts of things, someone else will offer top talent that. And you’ll lose folks even if you trained them.

This is logical for human behavior and prioritization. It doesn’t matter what field someone is in, they logically should pursue or seize better opportunities.

People who build and lead teams should automatically think about how they’ll retain anyone they train — how else will you recoup what you invest in people? Of course, how much you invest determines how long you minimally need to retain.

About managers: I have a high regard for great ones and constantly strive to uplevel those I manage and myself. That’s because managers can have the greatest impact on most folks’ work lives — good and bad. To me, no one should ever manage unless they fundamentally want to help bring out the best in people. How else is a manager supposed to produce maximum value?

Great management also creates legacy. Like if a manager teaches you a crapload, then you as a manager will be more effective for the rest of your career. You’ll be a role model for many others and that impact can continue well beyond you.

At the companies you've been at, how did you share/prove the impact of your content team to higher-ups, outside of traffic and revenue? And of those reporting metrics/stories that worked for you, which do you feel are the most underutilized by other content marketers? (No need to be specific by company, just overall)

Maggie: At face value, this seems like general stuff that you can google or get from GPT. I don’t have any genius answers to this that others haven’t covered, unfortunately.

I say that, because you can’t answer a Q like this well (AFAIK) without specifics. >> I can’t stress this enough: Different goals and content created to serve them require different metrics. <<The key thing is, be clear on why you’re creating which content and what results you hope to see. Like if you’re creating brand or TOFU content, don’t let anyone (much less your bosses) expect conversions, cross-sells, up-sells, etc. You can anticipate their disappointment if that happens.

It’s also your job to make sure that your team is clear on what results certain content is supposed to drive. Don’t let them keep proposing or creating content without clarity on business goals and relevant metrics.

What I’ve often seen when asked to advise companies on content: The content leader(s) themself (OK, not really a word) is not clear on the above. That then means their team often is producing a bunch of content, but not working on the right priorities. And because of that lack of clarity, their chances of being successful are low even before they’ve created any content. You can’t fix that in messaging to your bosses later, unless you say you screwed up and have learned how to better approach things. And you can’t keep using that tactic, haha.

What works for me: I strive to work for / with rational people. I don’t say that lightly. I screen employers for logical thinking. Why: If they’re not more logical than emotional, what chance do I stand of explaining logical things to them? So say some CEO tells me they want X results when I’m interviewing and I know those results aren’t attainable. I’ll tell them that and explain why. I gauge their reaction to see whether I’m getting through. If they don’t process what I’ve said, I’m not arrogant enough to believe that I can work some magic on them later. Some people have more charm and personality than I have (and maybe more patience), so maybe they can make that work. I don’t have that in me and I don’t even want to learn to work that way, because to me that’s highly inefficient.

One of the advantages (or privileges) that come with having a strong track record is that often execs will defer to you, trust that you know better than they do. That doesn’t help meanwhile, before you’ve earned such credibility, but I mention it to share possible light at the end of the tunnel. And at the end of the day, everyone will still expect business results.

On a parallel path, if you work at a company that cares about such things, this might help people see the value of your function:

Our content team at NerdWallet was known for its success across multiple measurements companywide: We had high retention, engagement, career development satisfaction, trust in leadership, etc. That was regularly measured across every team / function via anonymous surveys and we led as a team over years. And that happened even though ours was the only remote team for years. People across functions also worked closely with members of our team, because we were a horizontal team embedded with all lines of business and we also worked closely with other horizontal teams.

We constantly heard how content team members were great to work with — that we were highly collaborative as well as effective, that we took feedback well and strived to address problems. Other managers would ask us how to better manage, which is how I ended up coaching managers across many functions, for example.

All of that helped add to our value as a function. But I can’t imagine any of that having made a difference enough if we didn’t produce business results.

How did you approach building brand new functions or competencies on your past teams? Would especially be curious to hear about your process for building them when you didn't have experience in those areas.

Maggie: What can help:

• Do competitive research.

• Consume and compare thought leadership.

• Google the crap out of things. There’s amazing content out there for all sorts of stuff.

• Do all the above and THEN talk to people who’ve done it before. Why this comes last: Because you can ask smarter questions and get more from conversations with experts. Once you’ve learned on your own, you also can run your thinking by these people, so they can set you straight if you’re off. Or if you’ve consumed various content and have noticed oddities or conflicts, you can ask about them.

People often skip the solo learning, to their detriment. They miss out on deeper learning opportunities.

Of course, the Q you asked is broad, so the answers might vary, depending on what you’re going to be doing.

In my case, because I’m an exec, I can sometimes hire an expert in X and then learn from them in partnership. Like I just hired an events lead — I’ve never worked in events.

I also learned and calibrated when I interviewed events candidates. One of the Qs I ask when I intw people outside of my domain: Please tell me the difference between a good (whatever the role is) vs. a world-class one. I triangulate those answers and ask follow-up Qs.

Depending on what the domain expertise or SME is, that might be relatively easy or hard. Like if I had to hire a coder, there’s no amount of learning I can do with reasonable time and investment. In that case, I’d have to get someone who’s technical or whatever to help me with that.

You also of course should be looking at results when you’re building sh-t you’ve not done before. There probably are plenty of analogs in the world (or proxies) you can get hold of.

Examples of people I’ve helped hire or hired directly, even though I’m not from their domain:

• HR business partners
• Designers
• BizOps people
• Recruiters
• Social media folks
• Engineers

Like I said, I’m not technical, so I can’t check code. But I do know how an engineer is supposed to work with people from other functions, so I can dig into those kinda Qs.

In one case for example, I was the only non-product person who interviewed an engineer who was supposed to partner with my content team. There were about 10 of us on the interview panel and I was the only “no.”

Why: I flagged that the engineer didn’t know how to communicate strongly enough to draw out the right info to effectively push back on nontechnical people and collaboratively offer his expertise instead toward business goals, which is what’s valuable. The hiring mgr agreed to back-channel the engineering candidate and immediately two former managers said they’d never recommend him, because he sucked at what I’d highlighted and he contributed poorly.

I mention this, because some stuff, you already know and can apply, even if you’re not of the same domain. Don’t overlook that.

Also, depending on what you’re trying to build and who you have as coworkers, you can sometimes tap them. Like maybe put out a call via Slack and say you’re looking for folks with experience or exposure to X. In various cases, people will have such or they have network they might intro you to.

In my current stretch role, my C level boss has spent a lot of time upleveling me. That’s a privilege for me, but he also knew what he was signing up for. This assumes I will strongly out-deliver other people — presumably folks with X experience — that he could have hired instead. Having someone like my boss invest in me is quite expensive. It’s a bet on his part.

Depending on how strongly you’ve previously performed, some bosses will bet and invest in you that way. But this assumes that you’re not like a baby bird with its beak open, just waiting to be fed. You’re expected in parallel to be figuring out a lot of sh-t as well, independently and tapping your team and other coworkers, tapping other existing resources. Like at our company, there are craploads of documentation, other notes and decks, etc.

I joined ClickUp in January and I’m amazed by how much transparency and access the company offers, especially at 1k people and growing. To me, the challenge is what to prioritize consuming and learning, because there’s so much info. I’m like a pig in mud.

Any advice for someone starting a new head of content role tasked with building out a documented content strategy from scratch?

I’d need to know more but generally if I know I’m out to build a machine, I look at how to start building processes and documentation for anything we’ll need to scale. I’m not precious about any of those things and expect to rework or rebuild as we scale.

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