Want to Work for a Startup? Start a Conversation with David Gaspin

What does it take to work at a startup? Here are some insider tips from a startup recruiter.

Most people try to get through the job-search process as quickly as possible: apply, interview, get the offer, and, hopefully, be happy. Yet, for David Gaspin, his career revolves around using this process to match candidates to jobs, and help startups grow from the ground up.

“The most fulfilling part of recruiting is that everything you do has a real impact,” explains Gaspin, Senior Vice President of Human Resources for Delos, a wellness real estate and technology firm whose mission is to create spaces that actively contribute to human health, performance, and well-being. “It could be finding that needle-in-the-haystack candidate that matches that impossible-to-fill role, or it could be building out new learning, development, and onboarding programs that help our employees become more engaged, while growing their careers.”

Despite his passion for his job, Gaspin's career didn't start in recruiting or human resources. He started in another passionate industry: musical theater.

David Gaspin

“Like so many people, I moved to New York City with dreams of making it in musical theater and being on stage,” he recounts over the phone. After six years of gracing the stage and achieving his theater dreams, Gaspin decided to make the move into a more “grown-up” role and found himself working a temporary job with Conde Nast in their HR department, which eventually turned into a permanent HR Manager position. What followed were years of growth through various “people” roles that included everything from talent acquisition to more traditional human resources positions. After holding senior HR roles for notable companies like Conde Nast and Playboy Enterprises, Gaspin organically moved into the tech-startup life.

“I really fell in love with the vibe, the energy, the pace, and the innovation that was going on around technology,” he adds. “I then started to carve out my niche as a small-company guy.”

Recruiting for a startup vs. a large company

Currently at Delos, Gaspin creates and implements talent and HR strategies to develop the new startup, help identify business objectives, and hire talent. Yet, creating an HR and recruiting function for a startup is different than building upon an existing department in a large organization.

“You have more freedom [at a startup] because you're inventing things as you go,” Gaspin explains. “But the downside is that you don't necessarily have proven methods that work for this company. There's definitely a lot more trial-and-error when you're dealing with a smaller, newer company.”

Essentially, Gaspin starts from scratch, leveraging his experience working for larger organizations to tailor a recruiting and HR strategy for each of the startup's stages, whether he's hiring employee number one or 100.

What makes an ideal startup candidate? It depends.

Gaspin looks for different qualities in his candidates when he's hiring the first employees in a startup than when he's hiring the 30th employee, 50th employee, or 100th employee.

“In the early stages, you want 'doers,'" Gaspin says. “These are people who can wear different hats and who will just get things done — often things that fall into various job functions and categories.”

These first hires need to be willing to jump in and get their hands dirty for the good of the company. Once the startup gets into the 20- to 50-employee stage, Gaspin focuses on candidates with specific skills, based on the company's needs, i.e. customer service and marketing. Yet, they should still have that “doer” attitude, and be willing to roll up their sleeves to perform multiple roles. Once the company reaches 50 employees, it's time to add the strategic thinkers to lead teams. Then, once that 100-employee milestone is hit, the company needs to hire more experienced managers who can get the most from their teams and help with employee development.

In the early stages, you want 'doers'

“Invariably, this is where you find the most resistance since you have "Day 1" employees who don't necessarily want someone new coming in as their boss,” Gaspin comments. “But, if a company can get past this point organizationally, there's a good chance they'll be able to scale and find real success.”

Overall, the applicant trend that remains consistent among the stages is an emphasis on a “doer” attitude, another main difference between recruiting for large companies versus startups. While corporations focus on candidates with the specific skills needed to fill the role, startups need to find applicants who are confident they can do what's asked of them — even if it wasn't outlined in the job description.

“In a startup environment, being a jack- or jill-of-all-trades — or at least being willing to jump in and learn — can be invaluable to catapulting a career,” notes Gaspin. For Gaspin personally, he's looking for someone to consistently stay cool-headed and deliver in a hectic environment, possess the right attitude, serve as a team player, and exhibit “a level of confidence that doesn't cross over into arrogance.”

What Gaspin looks for in job applicants at a startup

Impressing the people who will ultimately hire you, or dismiss your application, is the main goal of the job search (besides landing the job, of course). Here are some resume and interview tips from Gaspin to help you succeed in the startup arena.

Tips for writing a great resume for a startup

When it comes to your resume, Gaspin wants to see clarity.

“I want to see an easy-to-follow narrative,” he explains. “I should be able to look at a resume and, within 10 to 15 seconds, understand your background from education to your first job to where you are today, in order to construct the pieces of how you got there and where you might go next.”

This means organizing your resume in reverse-chronological order to highlight your career path and demonstrating a track record of how you've “affected real change or produced results in past work,” highlighting times you have introduced a new process, suggested a new function for a team, or took the lead on a project; anything that goes beyond “checking the boxes” of your job description.

In addition, Gaspin stresses the importance of avoiding common job application deal-breakers that make professionals like him cringe. For example, there's nothing worse for Gaspin than receiving a resume that states the candidate is “detail-oriented” and finding the document riddled with typos.

Another mistake that frustrates Gaspin is when candidates don't take time to change those “fill-in-the-blank” areas in their cover letters — Gaspin estimates he's received more than 500 cover letters throughout his career that were addressed to the wrong company — 500!

“It proves that the candidate has no attention to detail and isn't genuinely interested in the job,” he adds.

Including your headshot on your resume is also a big no-no.

There's nothing worse than receiving a resume that states the candidate is 'detail-oriented' and finding the document riddled with typos.

“I have such a visceral reaction to that,” Gaspin laughs. While it may be the norm to include a headshot with your CV in other countries, it's considered a big mistake in the U.S. “If you're a U.S. native and still have your glamour shot in the corner of your resume, it leads me to believe that you think you're really good-looking or that including your photo is somehow going to help promote your candidacy — either of which is a huge turnoff.”

Tips for acing the interview with a startup

According to Gaspin, there are three elements he and his team assess during the selection process: can do, will do, and fit. Since he is not a subject matter expert in most of the roles he fills, Gaspin leaves the “can do,” or specific skill assessments, to hiring managers and others who are more qualified to judge the applicant's abilities. Instead, he focuses on evaluating each candidate for their “will do” and cultural fit. In the interview, he determines whether the applicant will have the energy, passion, and motivation to succeed in the role and company environment.

“I ask myself throughout the interview, 'Will this person be able to succeed at this company? Is this person going to be able to perform and excel here?'”

To figure this out, Gaspin asks each candidate specific behavioral questions and pays close attention to the person's communication style.

“I like to ask questions about what the candidate has done when faced with challenges similar to what I know they'll face in this role and at this company,” Gaspin reveals. Questions he likes to ask may include:

“Tell me about a time when you were asked to take the lead on a project or task without feeling like you knew the best path forward."
"Talk about a time when you had a new idea you wanted to introduce to your company. What was the idea and how did you go about getting it considered?"

When it comes to communication style, Gaspin wants to make sure the candidate's style will fit with the company environment. For example, for companies that are more casual with informal communication, candidates will need to shed their “interview facade” and interact in a way that would work well with the team, or they probably won't land the job.

Final thoughts

At the end of the day, Gaspin wants to see candidates that have “done their homework” on the company, created an easy-to-read resume, and demonstrated a level of confidence throughout the entire process. Bottom line: Be prepared, and you will make a positive lasting impression.

Interested in working with David Gaspin at Delos? Click on the following link to see their open positions, and follow Gaspin on Twitter for more career advice.

Want to Work for a Startup? Talk to David Gaspin