Scaling Fast? Here’s How To Think About Bringing Your Talent Along for the Ride

As your company grows, so do its needs. While a super tactical Product person is great at the seed stage, you’ll likely need someone more strategic by Series D. So how do you balance your current and future talent needs? Should you hire someone now who can scale through an exit? If you ultimately realize you need to hire someone over them, how do you manage that delicate process? And what are the shifts in startup worker expectations People leaders need to think about today?

I connected with Tak Nguyen, Managing Partner at Plenty Search, and Diane Vavrasek, Chief People Officer at Mojo, to discuss these questions and more. Want more advice like this? Follow me on LinkedIn to stay current with the latest People leadership news and tips.

Can you describe the persona of someone able to scale from Seed all the way through Series C or D?

Tak: If you’re looking to hire people who can scale with the company, the most important thing is “general cognitive aptitude.” Their domain expertise is less important than their intelligence and ability to grow.

Diane: I agree, and I’d add two more qualities: optimism and kindness. A healthy dose of optimism helps people maintain a positive attitude in the face of inevitable setbacks. And an ability to form meaningful relationships is so important to the fabric of a team.

Of course, there will be people who can’t scale and that’s okay. You need to have those courageous, honest conversations and, believe it or not, people are often relieved when you tell them it’s no longer the best fit.

What is some early evidence that someone will or won’t be able to grow with you?

Tak: View performance reviews not as a transaction, but a continual conversation over time. Make sure you’re looking at past and current reviews: If the areas for growth are consistent and not evolving, that person is not learning and growing.

Diane: If someone quivers when asked to do something outside of their job description, they’re probably not the right person for a scaling organization. Every single hire is so critical at early stages that someone who isn’t a general athlete is probably not a good fit—especially if they show resistance to flexibility early on.

How do you think about building the People team? How do you structure and resource it?

Tak: Benchmarking is really important: look at companies that are similar to you and figure out why someone would choose to work at your company instead. Then, optimize for the thing that makes your company unique and special.

Diane: I like the advice of Marc Lore, founder and CEO of successful startups including diapers.com and jet.com, who hires the Chief People Officer first. A CPO can help set the mission, vision, and values as well as bring in the best talent right away and ensure that DEI is incorporated into your processes from day one.

Let’s say you hire someone to lead a function in the early days, but they’re not the right person to lead at scale. How do you retain them? How might you go about hiring someone over them?

Diane: I always look to hire flexible people with a lot of humility who can more easily admit when they are in over their head. I advise managers to maintain an open dialogue at performance reviews so the employee understands where their gaps are and how to grow. The manager should be candid about their capabilities in the context of the company’s needs. For example, “We need these capabilities now and we think that you’ll take nine to 12 months to become proficient.  As you know, we need all aspects of our company operating at the highest level each and every day to achieve our goals. Since there’s a misalignment, we’ll have to hire someone above you.” Then, if you do hire someone above, make sure they’re AMAZING so your original hire can learn from them.

Tak: I see this as a four-step process. First, you need to investigate whether this person actually could be able to grow. There is nothing more demotivating than layering every single role, so look closely at the roles where you can invest in current talent.

Second, plant seeds. When you see gaps in their performance, mention it and coach them. If you do it correctly, they’ll realize they’re not hitting the mark and grow frustrated.

Third, make sure you offer an escape route. Talk about the benefits of layering, like opportunities to learn and grow and feel less frustrated, but give them a way out as well.

And fourth, include them in the middle or the end of the interview process so they feel their voice is heard–though don’t give them veto power.

How do you identify issues proactively, maybe even before the team?

Tak: Good people-hygiene processes, like regular performance reviews and surveys of employee sentiment. And make sure to bake in time to meet with individuals who you know will give you reasonable, measured, honest feedback on how the team is doing. This helps you keep a strong pulse on the organization.

Diane: Manager/employee one-on-one meeting hygiene is also critical, and these meetings should be more of an EQ check than a status update which can happen over Slack/email. I like to ask, “How are you doing? How motivated are you? How excited are you to come to work? What’s eating up most of your time?” These are great questions for skip-levels too.

Shifting gears a little to employee culture: What do you do when you have two very different work forces, such as knowledge workers and manufacturers?

Diane: Go back to your company values - these should drive what experiences, programming and policies you develop. At Jet.com, everyone got equity: Marc wanted everyone, from software engineers to fulfillment center workers, to feel like they owned the company. “Run it like you own it” only works if 100% of employees have ownership. The employee experience might look different across the company as there is no getting around the fact that a corporate office is different from a fulfillment center or manufacturing environment, but what you’re aiming for is to maximize employee impact and happiness  regardless of job title or pay band.

Tak: Hopefully the fundamentals are there in terms of comp and benefits, but it’s also important to use every opportunity to highlight the people who don’t usually get recognition, like the CX team or the fulfillment team. Everyone knows where their job falls on the totem pole, but don’t give anyone a reason to validate that they are less than another team.

Exchanging equity for pay cuts is no longer attractive to talent. What else has changed over the past five to ten years, or even since the economy has bumped?

Diane: Working models, like being fully remote, hybrid, or in-office . Every company is trying to figure this out.  For us at Mojo, having as many people as possible together in a room given our very early stage is important for efficient collaboration, ideation and communication so we leased an office very early on in our company’s existence...However, we balanced the legitimate health concerns some had with coming into the office by making attendance voluntary.  I do think for people early in their career not having face-to-face time can make things such as mentorship more difficult so with everything in life there are pros and cons to each approach.

Tak: The most important thing is having a deeply thought-out strategy. At a high-level, choosing to go remote will make hiring easier but community-building and collaboration harder, so if you go that route you’ll need to invest more in things like community-building and offsites. If you choose to do in-person, expect to invest 30-50% more in recruiting resources to achieve the same output in a pre-COVID environment.