Bootstrapper’s Guide to Hiring: Timing and Talent in Startups

Samuel DeCroes

Starting a new business or side hustle is exciting.

That’s why there is so much content online about starting one.

You’ll find endless strategies for monetizing every platform, from Etsy shops, YouTube channels, and Amazon stores to even Craigslist and Facebook Marketplace.

But, there is something few that influencers or marketing gurus discuss.

The Reality of Running a Business

Running a successful business takes prolonged dedication, perseverance, and hard work.

It also requires a lot of critical decision-making. The hardest of which revolve around staffing.

Decisions about when to hire (and fire) employees and how to efficiently manage operations are major sources of stress for most business owners.

Early in the business, mistakes in these areas will likely be catastrophic to its long-term viability.

So, ensuring the timing is right before you make your first hire is crucial.

What’s the Best Time to Hire My First Employee?

The best time to hire your first employee is when you start your company.

Businesses with startup capital, or at least some “substantial” funding, start with a combination of:

  • CEO,
  • COO,
  • CMO,
  • CTO,
  • CSO (Customer Success Officer)

Then, they hire people needed to fill specific skill sets.

But most small business founders and bootstrappers don’t have that luxury.

Instead, they often have strengths in marketing and/or technology and initially take on the roles of CEO, COO, and CSO themselves.

That’s fine in the beginning when the foundational pieces, such as the product, website, CRM, and email service provider, are being tested and implemented. However, when a company is successful and begins to scale, it quickly becomes unsustainable.

When you’re at the tipping point, the last thing your business needs is for you to become bogged down in technical issues or customer service problems.

What’s the (Second) Best Time to Hire My First Employee?

If you act too soon, you risk bankrupting your company. If you act too late, well, it may be too late.

Although the possibilities are endless, here are three common indicators you need help:

  1. Your product quality is suffering.
  2. Your customers are complaining.
  3. You don’t have time to deal with operational tasks.

Product Quality is Declining

As a one-person team, it’s impossible to notice everything. Mistakes happen.

Every typo, erroneous email, or broken link is a potential missed sale. It’s time to hire if these issues happen repeatedly.

The best person to find for this role is a copywriter or someone with a Liberal Arts background.

They’ll be able to help with your writing needs (customer service templates, daily emails, promotional items, product ideas) and can learn any specific reporting or technical needs the job requires.

That’s why copywriters make great candidates for your first hire, even if your product quality is not declining.

Customer Complaints are Piling Up

Creating and maintaining high-quality products takes tremendous time and energy. So much time that fulfilling the product can be difficult when you’re already stretched to your mental and physical limits.

Plus, a successful business naturally attracts a high volume of customer service inquiries.

Two hours per day spent replying to customers adds up to hundreds of hours over a year. It’s easy to fall behind. Then the customer complaints start piling up… And the business starts to spiral.

You can reduce customer service time with:

  1. High-quality products that fulfill your marketing promises
  2. Pre-written responses for your frequently asked customer inquiries
  3. Comprehensive FAQs for your website and products

But you should hire someone to help if you find yourself in the CS weeds, falling behind in replies, or unable to answer calls.

Hiring an in-house employee you can train and who will grow alongside your company is often the most effective approach for this position. Even if they are part-time, internally trained team members are almost always more productive and reliable than a call center.

That said, there are a lot of new startups in the customer satisfaction space, and it’s very easy and affordable to outsource your customer service. A simple Google search for “outsourced customer service” reveals many options.

You’re Overwhelmed by Office Tasks

Behind-the-scenes work, such as accounting, legal filings, paperwork, and random operational tasks, can accumulate. Because most business people are not accountants or lawyers, they put this stuff off or completely ignore it.

Don’t fall behind in these areas. Find a certified public accountant with good online reviews. A great CPA will make your company money over the long term. They can also help you with nearly all of your business filings.

Beyond a CPA, LegalZoom can likely handle the rest of your legal needs. Their services are diverse, and their customer service is extremely knowledgeable. You can also search for a business lawyer in your area with good reviews.

From 0-1, Without a Web Developer

As we’ve established, you don’t need a web developer to have a concept for a product and launch it online. But unless you are skilled in Python, understand JavaScript, and can navigate APIs, you will eventually need a developer.

The developer you’re looking for is called a “full-stack developer,” which means they can work on both the front end (user experience) and back end (data/processing) of the website. You should outsource the position if you have only a few tech needs.

Experienced developers with deep portfolios charge $150+/hour for their work. More affordable (but equally as talented) full-stack developers are easily found on Fiverr, LinkedIn, and Upwork.

Don’t just go for affordability. You need someone who can do the work well, hit your deadlines, and engage with you long-term.

Interview several candidates before you settle on one. If possible, assign a task to multiple developers to see who fits best. The best thing about outsourcing is the flexibility.

Bringing It All Together

The excitement of starting a new business is undeniable, but the real success lies in the ability to grow and adapt.

Compelling products, engaging marketing, and enjoyable customer experiences are critical for companies looking to compete in today’s flooded marketplace. But, creating and maintaining these elements as a solo entrepreneur or small team is a Herculean task that demands more than just dedication and hard work.

Recognizing the right moment to expand your team is a milestone and a critical step in ensuring your business’s longevity and prosperity.

Yours truly,

Sam DeCroes

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About the author

Specializing in digital marketing strategies and customer acquisition, I leverage my deep industry knowledge and innovative approaches to create campaigns that achieve results. Alongside Molly, my college sweetheart, we've made a home in the Greater Seattle Area. Surrounded by its serene beauty, I draw inspiration for my work, infusing every campaign with creativity and a unique perspective honed from years of experience. Read my full bio here.

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