You’re Not Ready for a Sales Hire: 4 Reasons
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Hiring a salesperson too early is a good way to distract your team and waste money. But there are three signs when it is time.

Do you work in a start-up? Do you look around every once in a while and say, “You know what we need? We need to hire a salesperson to really get this company off the ground?” Well, you’re probably wrong.

It’s strange for me, a lifelong salesman who started a company to help salespeople, to advocate not hiring one of my own. But that’s exactly what I’m suggesting, at least until you and your company are ready. Here’s why:

1. Salespeople need something to sell.

Some thing—not a concept or a prototype. In general, salespeople stink at product development. They excel at revenue development. If you are envisioning a great salesperson rounding up customers for your idea, your beta trial, or your brand new service, then you are dreaming. Good morning sunshine!

2. Salespeople are expensive.

The better a salesperson is, the more expensive he is. If a salesperson feels your product isn’t ready to bring to his contacts, she will hold back. Experienced salespeople are more protective of their contacts than the memory of their high school sweetheart. So for every day that your new sales gun thinks your product isn’t awesome, she is paying a big opportunity cost by working at your start-up. And she is going to charge you for it either in money or in frustration.

And if you find a salesperson who offers to work for equity, ask her how many times she’s blown away her quota.  Chances are she never has.  Don’t make the hire. If you do find the exception to the rule, that person isn’t in sales—she is a co-founder. Give her equity (that vests).

3. Salespeople are hopelessly optimistic.

If you hire a salesperson, he is going to run at the job like a pole-vaulter. He knows he’ll clear the pole. But it’s a rare salesperson who can keep the energy up if he doesn’t get quick, positive feedback from potential customers. After a couple of weeks of failing, most good salespeople are going to start thinking about other poles they could be clearing. And the ones that just want to hang on to the job? Well, there’s no quicker way to murder your company vibe than listening to your new salesman get dinged on 60 cold calls a day.

4. Salespeople are mostly risk-adverse.

Call it the curse of the fat bonus. A salesperson who has made $200,000 or $300,000 for a few years in a row is going to be counting the days until she can make that again. There just aren’t that many money-really-doesn’t-mean much-to-me-it’s-the-work-that’s-important kind of salespeople.

So please, don’t hire a salesperson to figure out what your customers need or whether they will buy some future product that might have some certain set of features. That’s the job of the founding CEO. Yes, it’s your job, even if you are an engineer.

How do you know that you are ready to hire a salesperson? Consider these three things:

1. There’s enough opportunity.

It will vary by company, but $1 million is the number I use. There has to be another $1 million in revenue that you can identify but that you cannot pull into your company because you are too busy selling to other people. If you can identify $1 million worth of prospects, it’s a great time to hire a salesperson.

2. Your product is awesome.

What does that mean to a salesperson? It means you have reference clients—paying customers who the salesperson can leverage. When she sees your customer list, you want her to think, “Oh man, if the founder can get these customers, I am going to KILL IT here.”

3. Your culture can handle an influx of sales energy.

If you have a tight, technical team, bringing in salespeople is going to change the atmosphere like a high-pressure system moving into the tropics. Batten down the hatches.

Hiring a salesperson too early is a great way to distract the team, waste your money, and bury a company. Hiring one too late means you won’t grow as fast as you otherwise could. It’s best to be on time, of course, but given the risks and rewards, it’s much better to wait until you, your product, and your company have reached some of the milestones I’ve mentioned. Then make that first sales hire.

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Grant Nelick

Associate

Grant Nelick is an Associate at Grit Capital Partners where he focuses on supporting the Investment Team in identifying, evaluating, and supporting investment opportunities.

Prior to joining Grit, Grant was a Venture Capital and Growth Equity Analyst at StepStone Group (fka Greenspring Associates). While at StepStone, he gained exposure to direct, fund, and secondary investments across varied stages and sectors. Notably, Grant worked closely on the early-stage direct and emerging manager fund strategies. Beyond his professional role, he activ ely invests in, and advises early stage companies.

Grant earned his B.S. in Finance and Business Analytics from the Kelley School of Business at Indiana University. He is based in New York City and Baltimore.

Topher Brewer

Partner & COO

Topher Brewer is a Partner at Grit Capital Partners. He leads capital formation and firm operations. Before embarking on the journey with Grit Capital Partners, Topher was the Chief Marketing Officer at ABR Capital Partners where he focused on capital formation, strategic marketing, and corporate development.

Topher’s professional journey is backed with invaluable experiences from notable entities, including Sands Capital Management, Facet, Brown Advisory, and Legg Mason. With a career spanning over two decades, he has been a stalwart collaborator for emerging investment sponsors, orchestrating strategies that propel exponential growth. Topher received his BA from Washington College. He lives in Baltimore, MD alongside his wife and two children.

Matthew Bellows

General Partner

Matthew is a General Partner at Grit Capital, investing in early stage companies across fintech, media and entertainment. Previously, he founded, led and sold three companies: a digital financial planning company called BodesWell (acquired by American Express in 2022), a pioneering sales enablement company called Yesware (Vendasta, 2022) and an early bet on the disruptive power of mobile games called WGR Media (CNET Networks, 2004). In addition, Matthew has served in executive roles at Floodgate Entertainment, CNET, Vivox, and American Express. Matthew earned his B.A from Naropa University and his M.B.A. magna cum laude from The Olin School for Business at Babson College. He is a long time practitioner and teacher of meditation, translating the power of mindfulness into modern daily life. He writes about startups, meditation, financial planning and cooking at bellowsand.co

Jennifer Byrne

General Partner

Jennifer Byrne is a General Partner at Grit Capital investing in companies in fintech, insurtech, and digital media. Jennifer has been an executive, venture investor, board advisor, and ecosystem builder in the media, telecom and financial services sectors for the past 20 years.

Jennifer co-founded Quesnay, a strategy and innovation advisory firm that delivered custom global startup accelerators with Fortune 50 companies in Financial Services, Technology and Media. Jennifer also launched the world’s first accelerator to source and support women-led fintech companies while facilitating mutually beneficial startup-corporate-investor relationships. Over 500 women-led startups have applied and been evaluated by 500+ industry leaders & investors, raising over $1.8B.

Before founding Quesnay, Jennifer served as VP, Business Development at American Express launching a digital payment service with global partners. At Verizon, Jennifer was Executive Director, Business Development & Partnerships where she was responsible for a $1Bn+ mobile applications & services P&L. She spearheaded Verizon’s innovation division, led 4G services launch, identified investment opportunities, and established industry-first mobile partnerships with Amazon, Facebook, Twitter, and YouTube.

Jennifer is a thought leader in fintech, and was named to the “Innovate Finance Powerlist” in 2020, 2019, & 2018 (+”Standout 35″), 2020 “NYC Inspiring FinTech Females”, 2021 “Female Founders Alliance Champions” & has been featured on the cover of AM Best and in American Banker, Nasdaq Tradetalks, FNO Insurtech podcast, Insurtech Connect, among others.

Jennifer is based in Santa Monica and New York, and is the co-cofounder of The Female Funders’ Club, the Duke University SoCal Career Chairwoman, and a mentor at TechStars. Jennifer is a graduate of Duke University and speaks Spanish, Italian, and French.

Kelly DeFelice

CFO

Kelly is a driven finance operator with over 15 years of experience working to build processes for companies from startup to IPO. Most recently she was running Sales Finance at Tastemade. Prior to that she spent seven years at Millennial Media working in various finance, chief of staff and sales operations roles, ultimately transitioning to Aol through acquisition. At Millennial she was heavily involved in IPO preparation and various M&A deals. Her areas of expertise include forecast and budget management, strategic sales planning, sales tool development, sales compensation and process development and improvement. She loves a good excel spreadsheet!

Jesse Leikin

Entrepreneur in Residence
Jesse is an entrepreneur and product leader with focused technical experience in ecommerce, analytics, and advertising technology. He has spent more than 15 years enabling digital business. He serves as Entrepreneur in Residence at Grit Capital Partners and leads the product team at Tradeswell. Having led development of SDKs and APIs for Millennial Media, AOL, Flurry and Verizon, tens of thousands of developers and platforms have used his products to manage their advertising and analytics solutions.

Mike Flannery

General Partner

Michael Flannery serves as both a General Partner at Grit Capital Partners, and is the Founder and Managing Partner of Redwood Partners and Redwood Technology Ventures. He focuses on technology investments in marketing technology, Fintech, and e-commerce. Some of his current investments include iFundWomen, Dubset, Alef, Measurence, and Jackpocket.

For over 20 years, Michael has advised global entrepreneurs, corporate executives and venture capitalists on strategic growth, talent strategy and executive search. Redwood Partners uses rich data and look alike success modeling to target and select talent for boards and executive operating roles. Since 2000, Redwood has operated an accelerator and has been successful making direct investments in seed-stage companies to compliment its deep experience in talent and venture development.

Michael is dedicated to the growth and acceleration of women entrepreneurs, and currently serves on the board of iFundWomen and the Female Entrepreneurs Fund. Michael is an alumnus and past Trustee of Cazenovia College. He splits time between New York City and Saratoga, NY where he resides with his wife and two children.

Paul Palmieri

Managing Partner

Paul Palmieri is the Managing Partner of Grit Capital Partners.  He focuses on data and AI based businesses in the areas of consumer software, marketing technology, media, and commerce. He currently serves on the boards of Niche and Incremental.

Mr. Palmieri is a successful entrepreneur in the internet space – most notably in the digital media ecosystem. He is the founder and Chairman of Incremental, who has pioneered neutral measurement for the fast-growing retail media space.  He was the co-founder, Chairman and CEO of Millennial Media (NYSE:MM) from 2006 to 2014, the market leader in mobile adtech. He led the company from being the early revenue engine for the app economy to catapulting into the programmatic media space.  In just 8 years, the company grew to 300M in annual revenue, operations on three continents, a successful IPO, and operation and growth as a public company (NYSE:MM). 

Earlier, he held management positions at Verizon (NYSE: VZ), Advertising.com (AOL), and Tessco Technologies (NASDAQ: TESS). He has been a frequent guest on CNBC, Fox Business, and Bloomberg Television, as an expert in user data, and the secular trend of mobile computing.

Palmieri is the former Global Chairman of the Mobile Marketing Association, and served on the board of the IAB (Interactive Advertising Bureau). He has served as a national judge for the EY Entrepreneur of the Year program, was a winner of the award in the technology category in 2011, and was named Executive of the Year in 2011 by the American Business Awards. Mr. Palmieri is a graduate of Mount St. Mary’s University. He is based in NY and Maryland.