Sasha Robinson, Trainual Head of People Ops, tackling our benefits strategy!

The Startup Playbook for Designing Your Benefits Strategy

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Sasha Robinson

October 22, 2020

Benefits are becoming an increasingly important aspect of compensation. And if you want to successfully compete for top talent (name a business that doesn’t), you need to think about your benefits strategy ASAP.

And basically, that comes down to figuring out:

  • What type of companies (and benefits packages) are you competing against during the hiring process? 
  • What type of candidates do you want and need to attract? 
  • How do you philosophically think about benefits at your organization?
  • What system(s) will you use to manage your benefits administration and employee experience? And who will run this on both the external and internal side?
  • How will you educate your team? (Hint: We use Trainual.)

Need help answering these questions? Here’s Trainual’s benefits strategy with a break down of my reasoning behind these decisions:

Let’s start with our benefits strategy

When developing Trainual’s benefits strategy, I wanted to make sure we were attracting and retaining candidates that would 3x, 5x, even 10x our growth. Meaning, I needed to secure top talent – every time.

But here’s the catch: top talent is typically already employed with really great benefits. So we needed to compete with big names that already had great cultures, teams, and products established.

For Trainual, our competitive advantage is our mission, our early-stage traction, and the honest to goodness joy of building something from the ground up. But that isn’t always enough. We couldn’t expect all these amazing future Trainual employees to join our team if it meant losing the benefits they’re used to.

So we had to be creative! And flexibility suddenly became the name of the game. How could our benefits package be everything to everyone we want on our team? Simply put, we needed options that were tailored to different profiles of folks at different stages in life, each with unique needs.

So, I infused this flexibility into all the benefits we’ve rolled out.

🔥 Tip: Dive deep into all the best ways to roll out your benefits with “Not Your Mama’s Open Enrollment” webinar!

Leveling up health insurance flexibility

Our benefits flexibility starts with our 4 distinct medical plans – with options for health savings accounts (HSA) or flexible spending accounts (FSA). And we even subsidize 100% of the employee plan and up to 70% of the family plan.

Plus, every employee has access to a RedirectHealth subscription – offering free primary care, lab work, and chiropractic care – and the option for dental and vision insurance.

Benefits are becoming an increasingly important aspect of compensation. And if you want to secure top talent, you need a robust benefits strategy!

But we also understand that some of our team members already have incredible health insurance through their spouses. So if they’d prefer to stay on their existing plan – great!

We still help cover the cost of their family coverage with our health insurance reimbursement program (up to $540 per month)! And about 25% of our team takes us up on this offer.

Regardless of whose plan they go with, we also offer additional “just in case” benefits to everyone for peace of mind. Short term disability, long term disability, life insurance, and AD&D included.

Going beyond just health benefits

But a solid benefits strategy goes beyond just health benefits. You also have to think through some of the squishier aspects like paid time off, parental leave, and work hours flexibility.

We’re a startup, but we didn’t want to foster the usual culture of employee burnout. So we knew we wanted a really robust paid time off policy. We offered unlimited time off for our first few years as a company. But most folks were only taking about 2 weeks off (between sick and vacation).

So we moved to a still generous 4 weeks of vacation, 1 week of sick, unlimited professional development, and 8 weeks of parental leave. And encouraged our team to start taking their time off by making most of it “use or lose.”

But this is only for legit time off. Need to pick your kids up? Hit a yoga class? See your therapist? We want our employees to do their thing – even if it’s happening between 9 and 5! All we ask is that they’re engaged with their projects, the team, and actually producing.

The flexibility in our physical benefits and with these squishier parts around quality of life is critical for attracting more senior candidates (especially ones with families).

Systems that manage top tier benefits

How do we manage all of these delightful benefits, you ask?! Well, for medical, dental, vision, short term, long term, HSA, FSA, life, and OneMedical, we use Justworks. And for 401k, we use Guideline.


Justworks is our HR system – it handles payroll, compliance, and benefits for us. But it’s also a PEO (Professional Employment Organization). Meaning, they have group buying power.

So Justworks handles all the headaches – like dealing with brokers and manual administration – while getting us access to more affordable rates.

So we get amazing benefits without the administrative hassle, and our team gets richer plans with lower premiums. Because of this, recruiting candidates from larger companies has not been a challenge for us. In fact, we’re often more competitive than the big guys!

And when open enrollment rolls around, employees can select their benefits in 2 minutes using their Justworks portal. Then, they’re all set. (An HR lady’s dream, am I right?!)

Meanwhile, Guideline is our investment management software.

So while it’s uncommon to see a 401k with a 3% employer match for company’s of our size, our CEO, Chris Ronzio, found that it’s a must. In fact, he first rolled out a 401k match when he had just 3 employees!

It was important to Chris that all of our employees had a vehicle for retirement savings. And because he wanted only the best talent for Trainual, it meant poaching employees from larger, more established organizations – where everyone gets a 401k.

And logistically speaking, Guideline has a 3rd-party integration with Justworks, so it’s a hassle-free 401k administration for our HR team. Phew.

Using Trainual to educate our team

We’ve invested our time and dollars into building a robust benefits package for our team – but that’s only part of our solution. Employee education (especially when it comes to what benefits they have) is critical.

But don’t just take my word for it! Our resident health insurance guru, Tori, wrote an extensive Trainual template called Health Insurance 101 about everything that anyone who has health insurance should know! And it covers all the basics, the most misunderstood health insurance terms, and has some tips to save your team money on health expenses!

👉 Start your free trial to get our Health Benefits 101 template. Already use Trainual? Sign in to add the template to your account.

We like to keep our benefits strategy as simple as possible. So we take care of our employees so they can focus on what’s important: their families (and life outside of work) and their work.

Admittedly, designing a benefits strategy for your company is hard. And it’s even harder for early-stage companies where raising funds means adding headcount quickly but efficiently.

But providing robust, yet flexible benefits has been critical in attracting the incredible team we have today. And when building your benefits strategy, having the right tool kit from the start makes building your business a lot easier.

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