The Unexpected Philosophy That Led Me to My Biggest Closed Deals Ever

Forget the conventional sales wisdom; if you go slow and steady, you can win a much bigger race.

8 min read

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As a startup entrepreneur, you may be acting as your own “sales team,” so you’ve probably noticed that we’re in a demanding time for sales. Even the artificial intelligence tools proliferating, to boost efficiency and productivity, can’t solve everything: Hubpot’s State of Inbound report, for instance, found 40 percent of full-time sales professionals surveyed saying that they’re having trouble just getting responses from prospects.

So, even though today’s automated tools can be a tremendous asset in helping us close sales more effectively, mostly they train us to think short-term. The common sales mantra, “Always be closing” comes to mind: This instant gratification mindset is great for racking up smaller wins, but what about closing that big brand deal that can forever change your business?

Related: 5 Reasons Every Entrepreneur Should Start in Sales

Turns out that closing that big deal is easier if you think of sales first and foremost as consulting with and educating the other person. Winning long-term customers requires showing them that you always have their best interests at heart and that you’ve put effort into finding creative ways to be a resource for them.

It means abandoning that “Always” sales mantra and adopting a new one. Here’s what I’ve personally found that that new mantra should entail:

Be more human.

The unexpected philosophy behind my biggest sales wins is this: Be more human. Add more value. Become a trusted source of knowledge to others by dropping the sales pitch and instead creating a lasting relationship.

Great opportunities are birthed from a little bit of luck and a lot of preparation and anticipation. You have to have that perfect cocktail — and the willingness to move mountains for a lead, build the relationship and take those lucky occasions to the next level — in order to see all possibilities.

Once, while at a conference in Boston, I took an UberPool to an event. One of my fellow riders happened to be in charge of employer branding for a top tech company. She asked what we do, saw value in my pitch and said I should stop by and talk more if I was ever in her city.

Soon after, I did find myself there for a conference and gave her a call. Fast-forward to a few years later, and that contact moved jobs to a Fortune 100 tech company in San Francisco. My company and its offerings had stuck in her mind, and we kept in touch with occasional outreach when I saw opportunities to add value.

Staying true to the mantra of “be more human,” I decided to use a gift-giving strategy by sending her a coffee gift card. I knew she had a particularly rough day looming and thought that she’d appreciate a much-needed coffee break. I paired this gift with continuous nurture by way of content, sending her new insights and articles that I thought she’d find helpful. These actions allowed me to stay top of mind with her and prove my ability and eagerness to help. By staying persistent and dedicating time to creating a relationship, I later closed one of our largest ever accounts.

I’d be the first to admit that this was not the most streamlined or instantaneous way to bring in new business. But in fact, the reality is that building relationships with your dream customers can take years. And I’m willing to devote that kind of time, because this “less efficient” philosophy is what helped me close deals with the executive in San Francisco and with some of the other biggest brands in the world.

Offer help for the sake of it.

When given the opportunity, offer help for the sake of helping. Adding value to a partnership is not always an easy task, but it shows that you care about your prospects as people, above all. This is a truly effective tactic that many of the most successful entrepreneurs utilize more often than you would think.

Manny Padda, president of EO Vancouver and founder and CEO of New Avenue Capital, shared the following advice on the EO blog: “Give, give, and give some more: The cornerstone of any real relationship is generosity — giving without the expectation of return. The best business networks are no different in that regard.”

A few years ago, an employee at a Fortune 50 company who registered for a webinar I hosted reached out because he needed someone to coach his partner network on content marketing. By agreeing to help someone out and be a reliable source without expecting anything in return, I ultimately won the opportunity to meet his team of global partners and pitch them on what my company does.

So, do as I do: Reject the “always be closing” mentality and the impulse to immediately look for ways to hit your quota. Instead, take on opportunities that may lay the groundwork for even bigger ones. If you hear a partner mention that he or she is struggling to find a solution to something, reach out to your network for advice. Help a friend out without expecting to be paid back in kind. Be available to people. These things can lead to a powerful outcome that benefits not just you, but your entire company. These are the memorable interactions that become crucial to long-term success.

Related: Want Higher Response Rates? Start Treating Your Sales Prospects Like People

Get visible in unexpected mediums.

In order to increase your exposure to new audiences, boost your credibility and create valuable relationships, you’re going to need to get visible in new mediums. Teaming up with partners in your network can create unique opportunities that benefit both brands in a big way.

Just look at the new ride experience brought to users by a partnership between Uber and Spotify. Uber users are able to enhance their ride by listening to their favorite tunes en route while Spotify has gained a new selling point to grow its customer base.

Co-creating through a trusted alliance is a clever way to give customers a new experience while delivering your message through an unexpected medium. That’s a good reason to keep your brain thinking creatively about how to co-create with valuable partners.

I personally discovered the value of this approach firsthand when the CEO of Technori, who hosts podcasts, invited me to co-host an episode with him. We had such a great time that he asked me to speak at a dinner with some impressive decision-makers from Fortune 100 tech companies, one of which ended up signing with my company.

So, take a leap! Do something you might not normally do. It never hurts to push your comfort zone and get involved with new mediums that allow you to share your knowledge and experiences with a new audience.

Use content for consultation and education.

I mentioned this earlier, but the main goal of sales should ultimately be to consult with and educate your leads and prospects. When you prioritize providing value and educating others over selling, you become a trusted resource who is thought of more often. One prime way to offer that education and consultation is through high-quality content that answers your prospect’s questions.

HubSpot is one of my favorite companies to use content like this (which makes sense because it’s what the company does). It has tons of resources in its blogs and email newsletters, and it releases insightful yearly reports with industry stats that help the company gain credibility because this content always provides unique value.

Another company that does an outstanding job with its content is the outdoor equipment company REI. When it comes to using content to educate the consumer on both products and what the company stands for, REI nails it. Its resources include a hefty blog, videos and podcasts, philanthropy and sustainability information and a how-to guide to all things camping. When you check out REI’s page, there is no doubt that you’ve found experts who are trustworthy, because their business is their real-life passion.

Related: 6 Psychology-Based Tips to Boost Your Sales

So that’s my argument: I challenge you to tackle your next sales opportunity with a little less urgency and to focus instead on being more human. Think of yourself as someone who can provide value without worrying about what you might get in return. The unforeseeable opportunities that evolve from this approach will amaze you.


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