Career 2.0: Recruiter

If you like connecting people and evaluating talent, becoming a recruiter may be appealing to you. This article provides insights and considerations around making recruiting your full-time profession. It is part of a broader series by Whispered on Career 2.0 options. 

While most recruiters have grown up in the search world (you’ll see familiar names as early training ground for many including SPMB, Betts Recruiting, add more here) there are many examples of top recruiters who have come from operating backgrounds, including:

Operating Background	Recruiter	Thoughts on relevance of background
Sales	Chuck Brotman Beth Gentile Andre deRussey Chloe Stewart Sisi Chen Koranda David Belden	Given the sales-cycles and relationship building these background often work well.
Marketing	David Cain Dan Weiner	Marketers are often challenged to shift to more of a sales-mentality

We are grateful to many of the people above for their help with this article

We love to learn of other former operators we can add to our list!

When could a career as a recruiter be right for you

For many senior operators, managing large teams can be draining after a while.  Some people love growing in responsibility and driving strategy / leading teams but others feel something is missing.

“I was making good money/successful in sales but always found myself seeking.  I was always helping people with career advice, even before I knew what I was built for.”  Beth Gentile  Former Sales Leader turned Recruiter

Many recruiters are natural connectors and get a taste for the business by helping others with their careers.   And…. the role of recruiter has many natural parallels with sales and marketing.  

“Both recruiter and sales/marketing are funnel-driven professions. They both start with large-scale awareness with a goal to convert and close the deal.  Recruiting is a sales and marketing job - just in the case of recruiting it is selling a great candidate on the company. Paired with deeper understanding of how GTM teams are built and function than a pure-play recruiter, I think recruiter is a great second career for well-networked GTM folks.”   Heather Doshay, Head of Talent at Signal Fire

What does the role of recruiter look like

This article focuses on the role of recruiter at a firm.  There are other flavors of recruiter (i.e. in-house recruiter, operating partner at a VC/PE firm and talent partner at VC/PE firm) but the 2nd career we consistently see GTM leaders succeed at is joining a firm

There are many reasons why companies don’t just post jobs and hire talent.  The fundamental model of search is a 20-35% fee on a hire’s first year compensation.  This ranges from:

• 20% on low end for contingent searches typically for less senior roles

• 30-35% on the high end for retained searches typically for more senior roles

Because of these high fees, 

• The recruiting business is by its nature a business of elephant hunting where you work very hard to source a search (if you are a at a firm) and then to find, vet and place candidates.  

• Companies often try to search on their own before hiring a recruiter.

Relationships are critically important to sourcing new roles.  Recruiters must be experts / love making connections and helping people vs. looking at it as a purely transactional business.  

There are many different types of recruiting business models with variances including:

• The type of commission structure:  Some firms are ‘eat-what-you-kill’ models while others share revenues in more of a pooled model to encourage collaboration.  

• Sourcing:  Some firms have built strong top-of-funnel sourcing and feed their searchers.  While this has many benefits it also means that recruiters at these firms don’t understand how the entire ecosystem works and would have a harder time going out on their own.  Other firms put the sourcing on each individual recruiter

Recruiting firms are very different.  You could be successful at one and not at another.”  Beth Gentile  Former Sales Leader turned Recruiter

Pros

• Built-in credibility with GTM talent: Your operator background gives you instant trust and insight when engaging candidates and hiring managers—people know you’ve been in their shoes - and you can help them avoid common mistakes.  

“The right recruiters with prior operating experience can help hiring managers think through the role, what success looks like, how to structure the process as well as other advice that folks without operating experience don’t really understand as they haven’t lived it.”  David Teichner, former operator turned recruiter

• Networking and connecting people:  If you love networking and connecting people, with recruiting, there is an opportunity to help nearly every single person in your network as every person is a) looking for a job b) knows someone looking for a job c) is hiring.

• Can build deep relationships:  Once you build your credibility with partners, you don’t have to sell - it is more of a conversation… but this can take time (see considerations below)

• Natural fit for outbound and rejection (for operators coming out of sales)Coming from sales, you already thrive on outbound efforts and resilience to rejection. In recruiting, the cadence is similar: repeated outreach, handled objections, and bouncing back after “no” builds a strong foundation. Outbound is the lifeblood of recruiting, and you’re already battle-tested. 

• Transferable sales skills (for sales operators): Identifying needs, pitching, negotiating are all crucial in recruiting. Many who pivot from sales remark that the hiring funnel mirrors the sales funnel.

• Learning new business models:  You get the ability to support the growth, and learn about the business models of many companies. In a lot of ways it is similar to working at a fund where you are evaluating / investing in a bunch of different companies vs one.

“I’ve seen folks who have operating experience love getting into recruiting as it offers them a bit more opp to flex their intellectual curiosity. You can be dealing with various models with various ICP’s in various verticals...on any given day. For the right person, that’s invigorating compared to working the same product, day in and day out.”  David Teichner, former operator turned recruiter

• Comfort with metrics and KPIs: You’re used to tracking pipeline and performance, these data-driven habits translate well to recruiter metrics like placements, time-to-fill, and retention rate. 

Con(siderations)

• High-pressure, undependable income: Recruiting can involve quota stress and unpredictability, especially with commission-based structures. You might have a slow year, not just a slow 2-3 mos, and you have to be able to weather that.  

• Long sales cycles:  Placements can take weeks or months—from sourcing to offer acceptance—requiring patience and long-term relationship management.

• Brand-building responsibility: Unlike structured sales roles, recruiters must develop their own personal brand, reputation, and niche in the talent market. Early days can feel like "selling yourself."

“You are selling you… not a company or product.  This can be motivating and terrifying at the same time.”   Beth Gentile  Former Sales Leader turned Recruiter

• Hard to build equity:   There is a motto that “Your next search is only as good as your current search.”   Firms can tap into flow quickly with investor relationships / specialties in hot areas but if you don’t keep doing great searches you can quickly lose your reputation.

• Can take a while to equal your income from operating:  It can take a while to build a referral base and earn profit-sharing from your firm.

• Market dependency: Your success is tied to hiring trends. Economic downturns or industry freezes can impact your pipeline rapidly.  There are often boom and bust years in search.

• Hard to pivot back: Once you pivot into recruiting, heading back into GTM operator roles can be difficult—you’re fundamentally changing career lanes.  

• Competing in a commodity business:  Unlike software sales (for example) where you have just a few competitors and likely nobody who can do exactly what you can do, there are hundreds of amazing exec recruiters who can help a company with a search.  Differentiating can be next to impossible (even though every firm thinks they are unique;) 

• Difficult to turn on sales engine for non-sales Operators: For Non-sales transitions (even Marketing), the idea of constantly focusing on BD, especially when it isn’t always a linear sales cycle, can be a challenging adjustment. Many aren’t successful at that part and it’s a crucial component. 

How you can become a recruiter

The path to becoming a recruiter isn’t well defined but here are some tips:

• Build relationships with recruiters early:  While you are still in your operating roles (when recruiters are working to build relationships with you) take advantage of this and build real personal relationships with them.

• Learn about the personalities of different firms:  Some firms hire former operators (i.e. Cole, Will Reed, RevelOne) while others (i.e. SPMB) do not ever.  Some firms provide help with searches, some don’t.  Prioritize firms you think highly of and help the with introductions.

• Join a firm vs. start on your own:  Given the lead-time to build your references (it can take you 6 months to ramp and searches can take 90 days+) it can take a few years to build a business.