Brett Ungashick, CEO & CHRO, OutSail

Brett Ungashick, CEO & CHRO, OutSail

This interview is with Brett Ungashick, CEO & CHRO, OutSail.

Brett, welcome to Best of HR! Could you start by telling our readers a bit about your background in Human Resources Software & Technology and what led you to this exciting field?

I started my career at LinkedIn selling their recruitment platform, LinkedIn Recruiter. To be successful in this role, I needed to develop a keen understanding of the world of an HR & talent leader.

Through this learning process, I was struck by how in-demand an HR leader’s time is. Whether it was the constant pull in different directions internally or the constant barrage of external salespeople and brokers, the HR leaders I observed seemed to have their attention requested constantly.

This planted a seed for me of a service I could start that eventually became my company, OutSail.

Your career journey in HR tech is undoubtedly filled with valuable experiences. Could you share a pivotal moment or project that solidified your passion for this industry and shaped your perspective on the role of technology in HR?

When I worked at LinkedIn, I cold-called a CHRO to try and sell our LinkedIn Recruiter product. I clearly caught this person at a bad time, as they gave me an earful.

I hung on the phone long enough to tell the CHRO, “I’m sorry. It seems like I caught you at a bad time. The reason I’m reaching out is simply because you have these open roles on your website, and they look like they’ve been up for a while. We have a tool that helps with this problem.”

The CHRO cooled off, and within two weeks, her company was a LinkedIn customer.

What this taught me was that the CHRO’s biggest pain point was not those unfilled job openings; it was actually that “salespeople won’t stop bothering me in the middle of my workday.” And that seemed to be a problem that very few people were solving.

In your experience, what are some common misconceptions companies have when selecting and implementing new HR software, and what advice would you give them to avoid these pitfalls?

The biggest mistake companies make in HR software evaluations is not being clear about what outcomes they are driving toward.

There are plenty of great systems on the market, yet each vendor has its own pitfalls and shortcomings.

The job of the buyer is to clearly define what their desired outcomes are and then keep those high-level goals top of mind throughout the buying process.

Ultimately, you will partner with an imperfect vendor, but if that vendor is strong in the areas that are most important to you, then you will have done a good job.

You mentioned previously that even with the rise of HR tech, service from these companies hasn’t kept pace. What are some key things HR tech companies should focus on to improve their customer service and support for their clients?

The truth of the matter is that HR technology and HR services are too complex for one vendor to deliver effectively.

Companies have traditionally looked to their vendors not just to provide software expertise, training, and troubleshooting, but they have also wanted the vendors to deliver strategic guidance and best practices to help them run their HR department.

HR has gotten too complex to administer, and technology systems have become too capable for any vendor to do both of these things well.

The modern buyer is understanding that their technology vendor needs to be a technology expert, and if they want strategic HR support, they need to look into HR outsourcing services.

You’ve worked with various businesses, from small startups to larger enterprises. How should a company’s approach to HR technology differ based on its size and growth stage? Are there specific solutions you’d recommend for each phase?

The size, complexity, and growth plans of an organization are probably the single biggest factors we look at when matching clients to potential HR technology.

For small organizations, you want to find a vendor that caters to companies of similar size. This would mean delivering a cost-effective, off-the-shelf system that can be administered easily without a heavy burden on a small team.

As companies grow, however, they will want to find a solution that allows for more configurability and tailoring. At this point, they will have more complex processes and workflows that they want automated and a larger team to help build those processes into the system.

Many companies are now dealing with a surplus of HR tools. What strategies can organizations use to evaluate their existing HR tech stack, identify redundancies, and create a more streamlined and efficient system?

We are constantly working with our clients to balance the age-old question: should we take an all-in-one or best-in-class approach with our technology tools?

My philosophy on the matter is: in a vacuum, fewer systems are better than more systems. Data is more consolidated, there are cost savings associated with bundling, and it’s better for the employee experience.

However, I do believe there are often great reasons for companies to layer in best-in-class point solutions. The two criteria that I suggest companies consider are:

(1) Is this point solution mission critical? For instance, a high-growth tech company probably wants a world-class recruiting platform.

(2) Is this disruptive to payroll? The further away a solution is from payroll (learning, recruiting, engagement), the less likely it is to cause significant pain from a data quality standpoint.

Looking ahead, what are some emerging trends or technologies within the HR software and technology space that you find particularly exciting or believe will significantly impact the future of work?

The biggest trend today is that companies are trying to figure out how to effectively manage a distributed workforce.

Remote work changed the game for employment, and it also created a significant burden on HR leaders.

For companies that are multi-state, they need to take on much higher compliance, state registration, and tax burdens. Are there going to be elegant solutions to make this easier?

Global companies need a system that can provide global payroll, EOR, contractor management, and global HR. This doesn’t currently exist in a single platform, but many vendors are trying to build it.

For HR professionals looking to stay ahead of the curve and enhance their understanding of HR technology, what resources or learning opportunities would you recommend?

Subscribe to smart newsletters across the industry. I think OutSail has a good one, but Starr Conspiracy and Josh Bersin are two others that I would recommend. Join a community like Resources for Humans, TroopHR, or CPOHQ. And attend events like DisruptHR and the HR Tech Conference.

Finally, what’s one key piece of advice you’d give to someone just starting their career in the HR software and technology field?

Try to deeply understand your customer as much as possible. The more you can empathize with the day-to-day challenges and frustrations that an HR or talent leader faces, the better you will be at delivering technology solutions to help them succeed.


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