3 Hires You Probably Need...But Might Be Too Afraid To Make
These change makers are needed now more than ever. Do you have the courage to pull the trigger?
Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators who have subscribed!
I’m your host, Bob, and my mission here is to share personal, behind-the-scenes stories of ups and downs from my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
Sitting in a role as a recruiting partner for fast-growing tech companies allows me to see different approaches to team building. It’s particularly fascinating to watch early staffing moves that start a chain of events that will eventually impact these businesses and their prospects for success.
I’ve noticed two new-ish team roles gaining traction among startups and an old one coming back into style. And as I look at companies that have embraced these roles, they tend to be the ones that are gaining traction despite these challenging times.
This post aims to share some insights on these roles and challenge you to look deeper into how they could move your team to the next level. And I do mean “challenge,” as inertia is a bitch.
Chief of Staff
You’ve got to admit, this is a pretty cool title. Maybe it’s the “Chief,” or maybe it’s because it’s something we’ve seen in real-life and fictional stories of the West Wing. Ironically, its power doesn’t come from having direct reports or budget dollars—and people can hold the role straight out of college or with 30 years of experience.
My first direct experience with someone in this role was at a startup that asked us to hire their first group of developers. The company didn’t have an HR person or an in-house recruiter. But it did have a Chief of Staff—who was one year out of college. She was a force of nature and is still one of my favorite clients.
I watched her work efficiently across her organization—herding the cats in the leadership team, running a clear interview process, and providing excellent feedback that helped us do our job better. She figured out office space, got bills paid on time, and ensured that the co-founders didn’t have to worry about how the sausage got made.
I wish I hired someone in a position like this during my last VC-backed startup. When on that path, a founder gets pulled into countless directions by the internal team and external clients, partners, and investors. The best founders usually aren’t great at tactical detail work, but the tactics are what often separates success from failure. A great Chief of Staff sits in with the executive team and is counted on to run with whatever is needed.
Over time, I’ve seen two types of people fill the Chief of Staff role. The first is like my client above: Take a fearless go-getter who isn’t too long out of an undergrad or MBA degree and let them drive action across the organization. While helping you get things done in the day-to-day, you’re also growing someone who can eventually take over a key leadership role in the business. They will see everything from sales to product to finance to client success and then “graduate” into leading what fits best with their skills and interests when the time is right. Oh, and have them hire their replacement before they leave!
(it’s also a role I wish I could have landed instead of paying for an MBA. Here’s more inspiration for you youngsters reading.)
The second opportunity is to bring in a senior leader with decades of experience in operating businesses—yet is no longer looking to rise the ranks or obsessed with playing power games. We all know countless men and women who hit age 50 or so and no longer want to climb the ladder, yet have a ton of energy, battle-scar wisdom, and a desire to keep adding value. By hiring these people, you bring in someone with the experience and range of a senior consultant who knows how to get things done from within.
Generally, the early-career person fits best with an early-stage startup where their very low pay and high energy help fill many executional gaps. The later-career hire is best suited for a company that has already gone from zero to one but is still growing and hitting the point of “knowing what they don’t know.”
It’s for when you need to upgrade organizational design—usually around when you start hiring managers of managers and get to the point where you don’t know the first name of every employee. They can also be “executives at large” whom you can trust to look at a new product idea or meet with a potential business. They fill the gaps around strategic direction, industry knowledge and networks, and culture-building. Plus, they can serve as the angel or devil on your shoulder with the courage to tell you when you’re screwing up.
Product Evangelist
The role of Product Evangelist has been around for some time in the software world, typically at companies that sell products or services to other software developers. These businesses need to get buy-in from the community of builders, so they hire a person who can carry the movement's flag.
Typically, the Product Evangelist knows enough about programming to be dangerous—they understand what developers think and have credibility with them. But the best performers in this role prefer the energy and excitement of leading a movement. They put on events, organize community groups, record podcasts, film videos, speak at conferences, and act as extreme networkers within the ecosystem.
They are more extroverted (than software developers…), passionate, and need to really, REALLY believe in the products they represent. But they can be very hard to find! Product Evangelists tend to fall in love with their products and those who use them. For this reason, from a recruiter’s perspective, they are some of the hardest people to pry away.
But, boy, they can be a force of nature. I think companies beyond software tools can benefit from recognizing these people and building roles for them. And you might be able to grow them internally rather than paying a recruiter like me.
Recently, a friend who leads a sales organization at a marketing-tech company told me about one of his sellers who has evolved into such a role. This new hire started as a junior seller in the company and did all the usual cold calls and conference meetups. However, he became increasingly interested in the company’s tech and industry trends.
This junior seller sent summaries of new products from Facebook and Amazon. He began networking with non-client thought-leaders in the space, leading him to meetings outside the usual lead-gen machine. Clients loved that he talked passionately about the space—even though he often forgot to hit the key sales pitch points.
He’s bringing in sales unorthodoxly, and now the company is working to put him into a new position that straddles sales and marketing. It’s not easy (see below), but it represents a role everyone should have: A person who is genuinely excited about the product+category and can fully focus on building trusted relationships in the community that eventually lead to sales—but doesn’t necessarily come with a quota.
Intern
First, let me admit that this is top of mind as I work with my daughter, Ella, who is seeking an animation internship before her senior year at Ringling College of Art and Design (any help is appreciated!!). In working with her and speaking with some of her classmates, I’m blown away by the skills and hunger of the rising generation.
I’m also a fan of interns because I’ve hired several throughout my career, including each of the past three years at our small business. At the early stage, basic work always needs doing, and a college student will bend over backward to take the grunt work in exchange for a reasonable hourly rate and a chance to put something—ANYTHING—on their resumes. Plus, you might find your next year’s hire.
At our last company, we built a robust intern program around the time we got to 30 employees. For both Client Success and Engineering, we always had bursts of work or special projects that interns could take on—if nothing else to help cover staff when they took a week off for summer vacation.
And the benefits of intern programs compound with time. First, when you find a strong intern, you can send them back to their senior year with an offer to join you when they graduate. It’s a months-long interview that results in top talent that gets off to a fast start when they return as a full-time hire. Often, they are game to continue part-time work when they return to school.
Second, they return to class and speak positively about your company. Fellow students and their professors put your company on the radar, and more top talent shows up at your career day booth each year. Suddenly you’ve got a talent pipeline of people who learned your way of doing business.
Interns also just bring a great energy and culture boost to your company. Even clients love seeing your interns join a Zoom call. We were all interns once, and we easily recall the struggle to learn about business and land that first job. It’s a joy to invest in their careers and to work in a company that believes in paying it forward by taking a chance on interns.
Get Over Inertia (and More)
Chances are that your company doesn’t have a Product Evangelist or a Chief of Staff, and you haven’t thought about posting an internship opening on your career page yet. Why? Well a lot of it has to do with intertia…We’ve never done that before; it’s important but not urgent; and we didn’t budget for it.
Let’s be honest: political fears get in the way, too. Who do they report to? Whose budget does this come out of? What is their place in the RASCI and the org chart?
Someone has to make the case, write the job description, interview candidates, build an onboarding plan, and establish success measures. And we’ve all got many other demands on our time, both at work and at home.
It’s not easy…but that’s why you’re a leader, dear reader. And as a leader, you have the ability to make the case, enroll help, and turn strategic direction into executional excellence. The job of a leader is to look at the organizational machine and see where new parts or finer tuning could make it produce more, quality output with less time and money input.
For some of you, this post will be a mental splinter. Once you delete this email or close this browser tab, your unconscious will keep processing. Tomorrow, your mind will direct you to talk with others about one of these roles. You’ll Google something about them or (God help you) search on LinkedIn for people you know with these titles. You might even write a job description…
How we might work together…
My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.
Need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups, and we love helping leaders turn their dreams into reality. We're the team our clients trust for software built to last.
Looking for Influencer Marketing and Content Creation? The team from our previous company is back by popular demand with A2 Influence. We’re ramping up now and would love to share more.
Feel free to schedule time together during my Open Hours for questions, feedback, networking, or any other topic!
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
A Splendid Exchange: How Trade Reshaped the World
As you consider reshaping your business with the roles above, I suggest you spare some free time to read about how trade reshaped world history. After all, most of us work in business, and all of us buy products sourced from around the world within hours. This book shares how we got here.
A Splendid Exchange walks through major moments in the history of trade. It is a fascinating look at the rise and fall of religions and kingdoms from the lens of exchanging goods for profit. You’ll see how globalization has been a much more gradual, longer-running trend than we might imagine. Here’s a great summary from its introduction:
“Ultimately, two deceptively simple notions anchor this book. First, trade is an irreducible and intrinsic human impulse, as primal as the needs for food, shelter, sexual intimacy, and companionship. Second, our urge to trade has profoundly affected the trajectory of the human species. Simply by allowing nations to concentrate on producing those things that their geographic, climatic, and intellectual endowments best enable them to do, and to exchange those goods for what is best produced elsewhere, trade has directly propelled our global prosperity.”