Scaling vs Coding: Should You Hire a Lead Engineer for Your WordPress Business?

Do you hand over the coding keys to a lead engineer or do you keep them? This is a question most technical founders will have to answer as their WordPress business scales. On one hand, you’re partially saying goodbye to a passion you’ve spent years nurturing. On the other, you’ll be launching into exciting new territories to build momentum for business growth.

There are many nuances to this particular decision, plus it’s a broad topic that I’m admittedly not too familiar with. To give me a better understanding of the thought process behind the should you/shouldn’t you, right through to finding and hiring a lead engineer for your WordPress business, I sat down with Freemius CEO Vova Feldman (who’s recently stepped aside from leading engineering himself).

But before getting into all that, technical founders need to first ask themselves:

How Big Do I Want My WordPress Business to Get?

Maybe you’re fine flying solo or having a small operation with three team members. Perhaps you have grander plans and you’re prioritizing expansion.

If it’s the former, good technical founders can easily stay in a lead engineer role while fulfilling other roles within the company. Things get tricky if you’re going with the latter — wearing many operational hats can quickly become burdensome once the team moves past five members. In all likelihood, you’ll have to sacrifice some of the time you allocate for various responsibilities. Because as the operation grows, there is simply more to deal with, and if you don’t hire people to deal with it, you’ll be the one that’s overwhelmed as new tasks and responsibilities arrive.

Whatever your growth goals (and pain threshold), you need to decide where to aim to live the life you want to live.

The Comfort Zone Versus Building for the Future

Circumstances, currencies, and countries differ. And many solopreneurs in the WordPress ecosystem are happy with earning $5000 a month if it can comfortably sustain their lifestyles. When there’s a small (yet profitable) user base, there’s not much support to deal with, you’ve got a stable product and returning customers, and you have the freedom to add new features as and when you see fit.

It’s comfortable. And there’s nothing wrong with that.

Problem is that adopting this stance means there’s a chance that similar products will appear to eat at your market. In all likelihood, these new players:

• Have agility on their side and the resources to capitalize on being a ‘young’ company
• Have a bigger team to push out features and updates (with a comparatively larger pool of funds)
• Have a potentially huge head-start — in a GPL open-source ecosystem, they can fork the market’s leading plugin and improve on it without going through the long product development process that solopreneurs typically go through.

Now let’s add agencies into the mix and the fact that they can easily fast-track themselves into the WP products market if they spot an opportunity. By nature, agencies are in the business of making money; they have the infrastructure and resources to bring in talented people to fill gaps in the business and scale quickly. As we attempt to leave COVID behind us, we’re also seeing outside investors enter WordPress to capitalize by purchasing smaller plugins/themes and gain a (progressively bigger) foothold.

Taking the above into account: can solopreneurs who’ve founded WordPress businesses afford to take it easy on product development and growth strategies?

Technical Founders of WordPress Businesses Need to Be Dynamic and Innovative

The WordPress space is increasingly competitive. This isn’t likely to change. In fact, from here on out you can expect more players to enter the market to claim their pieces of the pie. For this reason, technical founders who’ve been releasing product features casually will likely find themselves on the back foot, playing catch up against agile competitors. And what was once an untapped niche is now a populated market.

Logically, when your attention is pulled in all directions, product development will suffer. Where previously you could allocate 80–90% of your time to development, now you’re down to 30% and then to 10% because you’re having to focus on other areas in the business.

In relation to Freemius and the entrance of other (newer) software monetization platforms, this is something that Vova is keenly aware of:

In the software world, product makers can’t just stop developing. The ecosystem is dynamic; whether it’s compatibility with other products/APIs or new technologies to adapt, the changes are never-ending and there needs to always be some level of development happening.

You can’t expect to just provide support to grow your product. If there’s no development happening, you’ll see shrinkage. Even with subscriptions, every month the revenue will drop. Eventually, your product will die. Technical founders can’t afford to let themselves get below that 30% capacity … even if $5000 is enough for your lifestyle. You have to innovate and adapt to stay relevant.

So innovation is non-negotiable (especially in the current climate).

But business dynamism takes deep thought, planning, and execution. It takes time. And this is something founders will find lacking if the business is growing — things just have a way of piling up if you don’t have contingencies.

At this stage, technical founders (and founders in general) will likely reach a crossroads…

Which path will you take?

Staying on as Lead Engineer or Taking Up the CEO Mantle Full-Time

It’s inevitable that leading both the company and engineering will take a toll once you move past five people. Even the most ambitious technical founder will struggle to string together consecutive 14-hour working days.

As the responsibilities pile up, you’ll inevitably become the bottleneck.

How to Know Which Role to Choose to Scale the Business

• What’s taking the most time?
• Where can you remove yourself to expedite progress?
• Pre-sale conversations or building new product features — which genuinely pulls you?
• Where do your true interests and priorities lie?

You need to be honest with yourself when answering these questions.

If your passion for coding means you can’t let go of development, one option is to find a COO or co-CEO to take over the operational side of things, such as marketing and business growth strategies. This allows you to stay on as the lead engineer without having to necessarily hire new WordPress developers in the immediate future.

It’s also affordable to hire a junior WordPress developer for a trial period to take on technical responsibilities like customer support. Once you’re satisfied with their progress, you can assign them more responsibilities incrementally, with the aim to nurture them into a full-time position when you believe they’re ready. As a junior will typically have less experience and a lack of bias, you can shape and mold them in a way that’s most suitable to your engineering needs. Who knows, maybe there’ll come a day when they’ve progressed enough to take up the lead engineer mantle themselves?

That said, both of these examples require a great deal of mentoring and training (when scaling operations should be one of the main priorities). There’s also no guarantee that the junior developer will grow into someone who can potentially hire for and lead your engineering team. Likewise, the COO/CMO/co-CEO you’ve brought in to champion growth strategies may not be a good fit after all.

From team management to finance and hiring, founders need to deal with so many other operational duties that aren’t related to coding. Again, you need to be honest with yourself — are you a top-tier lead engineer who can take product development to the next level? Or will the business be better served by handing the keys to someone technically better than you?

After some honest soul-searching, let’s assume that many of you would choose the latter.

How to Hire a Lead Engineer for Your WordPress Business

Essentially, you’re divesting yourself of engineering responsibilities so that you can focus on business growth.

In your stead, a super-skilled WordPress lead engineer needs to step in and advocate for engineering excellence. It’s a mission-critical role (second in importance only to yours) and this person needs to be excellent across the board — from engineering to managerial and communication skills.

In essence, you need an engineering superstar 😉 And they should be better than you at the technicalities of coding.

Think about it: if you have superior coding skills, since you care, you’ll have to consistently step in to review your lead engineer’s work and vet their decision-making. This is instead of getting into the higher-level responsibilities like directing your team and business along the growth roadmap you’ve laid out.

If you find someone who’s better than you are, fairly quickly they can jump in and handle the engineering priorities (and the team if you’ve already got one in place). The majority of engineering responsibilities are no longer on your plate! Sure, you’ll still need to guide them and communicate your expectations. But bringing a lead engineer superstar onboard really frees you up for other growth activities and opportunities.

Vova adds that your hire doesn’t necessarily have to be the best engineer in the world, either. They should, however, be in the top 1% if you are aiming for excellence and want to have your engineering in good hands that you can trust.

Luckily, numbers are on your side — there are tons of excellent engineers around the world. But finding ‘superstars’ who are looking for new opportunities is another story. Professionals at the top of their game usually don’t go looking for jobs … the jobs find them.

But I’m getting ahead of myself. Likewise, you may want to curb your enthusiasm before casting the net for candidates. First, you need to get granular and:

Drill Down Into the Lead Engineer Role and Responsibilities Thoroughly

Leave no stone unturned as you map out your expectations for the role.

Founders must know exactly what’s required so that they can communicate the details to candidates. This is beneficial for both parties as it sets precise expectations from the beginning.

Some thought-starters for the job spec:

• Technical responsibilities, both day-to-day and ongoing
• Managerial responsibilities, including team development and growth
• Product development milestones, including new features output that plug in (ha!) to the ‘big picture’ milestones

As the position takes shape on paper, many founders will find they’ve been responsible for multiple technical roles.

And I’m sorry to say, but it’s unreasonable to expect a top-tier engineer from a large company to jump through hoops and perform multiple roles for a bootstrapped company. Passionate employees will go above and beyond … but above and beyond for 12 hours a day, most days of the week? Don’t think so.

This puts a buggy spanner in the recruitment works… or does it? Vova expands on the point, taking a pragmatic (and positive) stance:

As you said, there’s a good chance technical founders will find that they need multiple people to replace them in engineering. And that’s okay, right? If you hire a lead engineer who can cover 70–80% of the needs, that leaves just 20–30 % of leftover responsibilities — that’s fine for the short term and until your lead starts hiring new developers.

You’ll figure it out. But even taking 70% of technical responsibilities out of your hands is already very meaningful. Suddenly, you have much more time to focus on growth and other mission-critical activities. And in parallel, you have a team member that is dedicating 100% of their time to engineering, which can go to infrastructure, testing, and closing the technical debt you kept postponing for years.

How to Find a Good Fit (and Not Tank the Opportunity)

As with other leadership positions, technical founders need to have strong chemistry and share common values with their technical leads. A shared belief in the future of the business will ultimately create a better product and a stronger team, from top to bottom.

But first, bootstrappers will need to identify these talents out in the wild. And it can be tough to find your ‘trophy’ when they’re so good at hiding themselves…

Discovering the ‘Hidden Gems’ of the Engineering World

Remember when I said I was getting ahead of myself? Well, we’re all caught up and I’m going to let Vova take it from here:

Once ‘superstars’ are in the work cycle, they won’t be looking for jobs — jobs (or recruiters) come looking for them. Everything is moving to tech and the demand for engineering talent is crazy. If you’re good, you’ll be chased.

So if you’re looking for an engineer to head up development in your WordPress business, you’re probably not going to find them using the regular recruitment channels. You need to actively recruit — actively search — for these hidden gems who aren’t working, or aren’t satisfied with their current role, or who haven’t put themselves back on the market yet.

In our discussions, Vova often highlights the benefits of networking and building relationships with other entrepreneurs. Building connections can be enriching because these conversations can challenge you and open your perspective to new ideas and ways of thinking/working. This practice also extends your network in a meaningful way.

And it helps in this situation too. The more people you’ve connected with, the greater the chances you’ll know someone who knows of someone interested in new engineering adventures.

If you’re lucky, maybe you already know someone that you feel is a good fit and they’re bored at their job and looking for something new.

As a start, message your acquaintances (high school friends, college buddies, etc.), nudge your peers, and put the word out that you’re looking to hire a lead engineer for your WordPress business.

When you do identify a potential ‘superstar’, I’m afraid to say that — in most cases — the battle for their talents has only just begun 😉

Alright, it’s not that dramatic! But cream-of-the-crop professionals, who’re pretty high on the ladder, will presumably need you less than you need them. Technical founders of WordPress businesses need to be sensitive to this — concessions need to be made — because financially speaking…

Bootstrapped Companies Can’t Compete With Big Tech (Google, Amazon, Apple, Meta, Microsoft)

Especially in an open-source ecosystem like WordPress.

But a great engineer can easily be worth more than ten mediocre ones (maybe more). So founders need to find other ways to convince these top-tier high-earners to join them for less than they’re used to.

Right off the bat, Vova says:

‘Don’t Be Cheap!’

Squeeze your budget as much as you can to offer the highest salary you’re able to.

And I would say it’s not only in the case of a lead engineer but with your leadership team too. You want these people to be dedicated … to be with you for the long run. It’s challenging to find great people in the first place, so you don’t want to tank those opportunities before you’ve even had a chance to explore them.

You don’t want to lose out because you could have paid $1,000 more, but chose to negotiate instead.

Even so, putting your budget in a proverbial vice — twisting the lever until it can’t go any further — will not squeeze out a number that can compete with the giants. So what’s a solopreneur to do?

Find Meaningful Compensation to Augment Lower Salary Numbers

Before COVID-19, WordPress business owners had an ace in the hole in that they could offer remote working as a benefit. The pandemic changed all that and the flexibility of working from home/hybrid working is widespread now.

Fortunately, there are other ways to persuade candidates to join if you can’t match their current salaries. These reasons can be value-based, growth-orientated, or offering them the chance to do work that excites them. For example, a return to nitty-gritty coding with newer technologies than the comparatively old and stale software stacks that big corporates generally use.

But none of that is compelling enough if the candidate doesn’t buy into the mission and vision of your WordPress business.

Link Their Aspirations to Your Value Proposition

You as the founder need to become good at selling the story of your company. You need to make them as excited as you are for what you’re building, and are going to build in the future. The company values and product priorities you share need to be really meaningful, especially if your potential lead needs to cut their salary.

Focus on this first, rather than the technicalities of the position … you can get to those when discussions become more serious. It’s a huge challenge because we’re in a plugin/theme space where typically the technological part is not so exciting, but it can be done.

There’s more to it than just pitching the values and mission of your company. You also need to identify their aspirations. Tap into their ‘why’ in a significant way.

Maybe the lead engineer is sick of being a cog in a big, slow-moving machine. Or they miss the days of hands-on coding and pushing out features for a product they believe in (I go into detail about this in the next section). Perhaps they want to get in on the ground floor; to be an integral part of growing a small company to big success. Maybe their ‘why’ isn’t even related to business but is something more personal. A hobby for example:

Let’s say you have a gallery plugin that targets photographers. A superstar engineer who’s also a photographer hobbyist may relate to the problem you’re solving. Therefore, they’ll have a bigger motivation to work on something that helps others like themselves. I.e. a personal connection to the company’s mission. This is true for any vertical: when someone relates to the mission (even better through a personal passion for the problem it solves), they’ll be more open to compromise on salary and other benefits for the sake of the mission.

Open a window into your business and let the candidate peek in to see if the core of your company resonates with their aspirations. If you look at it clinically, you’re using your value proposition to address an important pain point for the candidate, be it professional or personal.

Tap Into the Lead Engineer’s Passion for Coding

In comparison to bootstrapped startups, the cogs in a large corporate machine tend to move slowly. As an engineer moves up in the ranks, the less ‘hands-on’ their position becomes. Managerial responsibilities and high-level decision-making take priority. Things get more regimented and less exciting coding-wise.

Any good developer loves to code. It’s a passion. An art form. And it’s what got the vast majority of you into engineering.

When that passion is largely moved from your day-to-day, boredom and dissatisfaction can easily set in. In my mind, it’s akin to having the writing component removed from my job. I love writing (please don’t take it away from me 😅)

Tapping into an engineer’s love of coding can be a compelling selling point, as Vova explains:

Open your eyes to people who have hands-on experience; maybe they’re in a corporate position where things are slow … they feel small and want to have a bigger impact.

Pitch it to them that they’ll be getting their hands on the code again — building awesome things and also using modern technologies. For us, that’s where the fun is.

But as we all know, business isn’t just fun and games, and even the coolest coding projects can lose their luster in the face of a lengthy interview process.

To Interview … or Not to Interview

Generally (myself included), people don’t like to go through the interview process. It’s a high-pressure situation and there’s no certainty that it will lead to anything concrete.

This is especially true for engineering leadership positions, where the process can go on for a month or more! That’s tons of unpaid work, probably done after hours too. Moreover, hiring a technical lead typically involves five/six interviews that test (and tax) a person’s technical, managerial, and soft skills.

Many technical leads at big companies simply don’t have the time or energy to go through the process again. Founders need to be sensitive to these concerns and willing to make compromises.

Forgoing the Lead Engineer Interview Process

This is one of the reasons it’s so important to start talking with people early on. Even if they aren’t looking for a job right now, you don’t know where they’ll be in three months. Things change, and when they do, you’ll have an established relationship. If you have a positive chemistry with a potential candidate and your story is compelling to them, that’s a lot of the foundational legwork done.

But if you want them more than they want you — and they’re still willing to give it a try — you may need to cut them slack with the interview process. This is assuming you trust their background and have some previous acquaintance with their success.

Right, so you’ve agreed to jump straight into a trial period. What’s next?

It’s up to you as the founder to be explicit about your expectations. This means:

• Being clear about the trial period’s duration
• Selling the concept as an opportunity for both sides to evaluate the situation
• Creating a realistic set of KPIs with which to evaluate their performance
• Ensuring that your lead knows that they will still have to prove themselves, regardless of how good they are

Of course, diving straight into a trial period runs the risk of wasting time on training if it turns out to be a bad fit. But these are just some of the concessions that need to be made to grow a WordPress business successfully.

For founders wary of entering a trial period ‘blind’, there is the option of agreeing to it on the condition that a soft skills interview takes place. It doesn’t need to be long — an hour, an hour and a half — and it will help you understand their management style, how they communicate, and any general preferences they may have. More on that later.

What Happens When a Potential Superstar ‘Chases’ You?

Before I move on, I’ll briefly touch on what happens if you’re the one being chased for a leadership position at your company. I say brief because it’s rare to find a superstar this way. Founders with good products and growing businesses will be no strangers to candidates reaching out to them. The majority of these conversations won’t lead anywhere. But now and then, an engineer with genuine potential — one who believes in the vision and mission of the company — will make contact to start the conversation.

But eagerness and enthusiasm can only go so far. And if you don’t have an established relationship with the candidate, you’ve no way to gauge their expertise or experience. Regardless of how impressive their LinkedIn or resume is. And no, inspecting the code of plugin(s) they’ve developed is not enough. It will give you some insights into their coding practices, but as most plugins are pretty simple it’s not enough to evaluate whether they have what it takes to lead your engineering.

Here, founders need to be as thorough as possible. Take them through the entire interview process like Google or Microsoft would — be meticulous about testing their technical, managerial, and soft skills. Leave nothing to chance because you are still essentially strangers.

What Soft Skills Should You Look for?

There’s no hard and fast rule here. The soft skills you’re after are dictated by your personality, values, and business priorities. There are also the needs of your audience to consider.

For example, are you looking for a WordPress lead engineer who prioritizes pushing updates fast over a perfectionist who agonizes over every detail? Do you want an engineer to nurture and grow a team of developers or one who will take on the bulk of development for the foreseeable future?

It’s up to you.

Obviously, there are general requirements that are non-negotiables in distributed, remote-friendly companies:

• Intelligence! Creativity! But this is true for every role
• Excellent communication skills, especially over text because that’s how most of the conversations take place in distributed companies
• Trust, while not a skill, is 100% expected and needed between the founder and technical lead
• Autonomy, self-discipline, and the ability to manage their schedule
• A passion for what they do. In this case, they should love coding!

But what if good chemistry, optimizing for the highest salary you can offer, and ditching the interview process aren’t enough to sway the heart and mind of your engineering superstar?

A Vested Interest Can Be a Powerful Motivator

In the WordPress space, it’s super rare for single founders to give team members a stake in their company (let alone to outside parties). There’s a mentality that, since it was bootstrapped from the ground up, it’s the founder’s baby. And theirs alone.

Maybe there’s an irrational fear of losing control of the business — I’m not sure. But just think of the impact a highly experienced lead engineer could have on your WordPress business.

People don’t realize that there are mechanics to offer ownership which still protect you and your business. You don’t necessarily have to give a percentage of your actual company away.

So what can founders put on the table to be extrapolated as a stake in the business in the future?

How to Use Vesting to Bring Experienced Talent to Your WordPress Business

Liquidity events make it difficult to hand out equity. But as Vova says, other financial mechanisms can be extrapolated as a stake in the business, such as ‘options’. An option is a contractual right held by the grantee to purchase a capital interest in the company at a fixed price in the future. Once in place, founders can implement measures to protect themselves from having to hand over equity following incidents like premature resignations.

One such agreement is a vesting contract.

Vesting splits the stake percentage over multiple years. For example: if the stake is 2-5% (a benchmark for an early-stage startup CTO), your lead engineer will only be able to accumulate the full percentage over four years. If they choose to leave the company after a year, they’ll only receive a quarter of the agreed-upon stake in the company.

And to safeguard yourself from sharing options in case of a bad fit, or someone who decides to ditch early on, adding a one-year ‘cliff’ is a common practice. If your technical lead opts to leave before their first year anniversary (or you decide to let them go), they don’t receive any options. If they stay, however, they receive their vested options as agreed.

These agreements can protect founders and offer a strong psychological motivator for lead engineers to commit to the company and its vision.

Ultimately, the Top 1% Raises the Value of Your Company

The ‘equity math’ is much less of a headache when you recognize that bringing exceptional talent to the team raises both your company’s reputation and its value, which is important when you undergo an acquisition.

In the startup world, investors don’t like to put cash into companies with a single founder — the chances of company success are significantly lower. It’s better to have multiple founders or at least multiple people that have a stake in the company.

Giving a few percentages of your company doesn’t mean you’re giving up control. Just imagine the potential impact on your company when you bring someone who is technically better than you are; someone who can dedicate 100% of their time to engineering. This 1% or 2% that you ‘give up’ can eventually double the value of your company, making your 98% worth 196% of what it’s worth today.

This small sacrifice — along with the compromises and concessions mentioned throughout the article — gives you a better chance of finding someone exceptional. This in turn means your WordPress business is better set up for growth, longevity, and success.

You deserve it. And so does your maturing bootstrapped business.

What We Have in Store for the Freemius Engineering Team

And now for a peek behind the curtain…

It’s been really exciting to see the Freemius engineering team hit its stride over the past year and a bit. There’s been a huge amount of traction in recent months, and each new member has brought unique talents, styles, and practices to the development palette, resulting in a surplus of awesome new features and functionalities:

• Developer Dashboard: Custom localhost URL patterns, refunding without fees, subscription cancellation coupon, and more
• Affiliate Dashboard: Affiliate links store attribution, new Affiliate Dashboard, and more affiliate platform enhancements
• User Dashboard: UX improvements, downloading product versions, account closing, and Help Scout Docs integration
• Misc. Enhancements: Selling static products, email deliverability issues notifications, and boosting WordPress.org reviews

I’ll leave the (almost) last words to Vova:

As a technical founder who’s chosen to handover the engineering team keys, it’s been super fulfilling to watch new members find their footing and contribute to the forward momentum. Sure, there was a period of training Freemius’s lead engineers (in fact, training never stops), but each day sees me becoming less of a bottleneck and more involved with other growth duties.

And the good news is that we’re still on the lookout for engineering talent. Specifically, for a WordPress developer and a senior PHP developer. So, if you’re that person or know of someone who could be, please apply through the role links.

Here’s to finding your lead engineer superstar and I wish you further growth and success in the future!