Wanna get ahead? 8 sales leaders share their secrets to success

We spoke with Chicago sales leaders about the secret tricks that help them succeed.

Written by Andreas Rekdal
Published on Feb. 22, 2018
Wanna get ahead? 8 sales leaders share their secrets to success
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“Be like a duck.”

That might not immediately sound like sage sales advice, but to Anna Frazier, who is tronc’s Chicago Tribune director of sales, learning from the water bird’s subtle perseverance is the best thing a salesperson can do for their career.

We spoke with Frazier and seven other Chicago sales leaders to learn more about the secret tricks that help them succeed. From preparing extensively to knowing how to turn a quota into a strategy, here are the best pieces of advice we heard.


tronc chicago tech company
image via tronc

The media company behind brands like the Chicago Tribune, New York Daily News and the Baltimore Sun, tronc has an in-house team tasked with building technology to push its digital content distribution and monetization strategies forward. Anna Frazier, who is tronc's Chicago Tribune director of sales, said the best advice she ever got ties back to the animal kingdom.


What is your secret sales weapon?

One of my mentors would always say, “Be like a duck.” On the surface, a duck glides gracefully and calmly. Beneath the water, though, a duck’s feet are working a mile a minute, battling the current and accelerating that duck in the right direction. Salespeople need to show that calm confidence to prospects and clients, who should never know the pressures of quotas or monetary concerns that go hand-in-hand with the potential close. This makes people want to buy from you and makes people want to follow you!

Moreover, have you ever seen water land on duck feathers? It rolls right off their backs. So many times, sales reps and leadership get bogged down with the office politics or distractions within a sale. Great salespeople don’t let those things get in the way of success. Be like a duck, close the deal and let everything else just roll off your tail feathers.


How do you pitch tronc to top-flight sales candidates?

Culture is everything. Tronc puts a big emphasis on your career path and internal growth. We have evolved our internal sales team to give our employees a traditional path while encouraging a self-starter mentality. I share multiple stories of salespeople significantly growing their skills and sales when they join our company. I may even share my own story of career development and how this company always encouraged me to strive for more. I came to tronc to become a part of something bigger than myself, and I want all potential candidates to know that same culture is awaiting them if they want to join us!


sprout social chicago tech company
image via sprout social

Sprout Social’s software lets marketers manage social media strategies across all their channels, offering in-depth analytics about how customers engage with them. To sales development manager Jenny Poore, success is all about setting goals. Few sales reps cite quotas as their favorite part of the job, she said, but high performers find ways to break quotas into daily action items that help move the needle.


​​​​What is your secret sales weapon?

Tackling an ambitious monthly quota can be one of the most overwhelming aspects of sales, no matter what stage you are at in your career. It's really easy to feel the pit in your stomach form as the first business day of the month approaches, but I find top performers are able to combat this by breaking down their quotas to create daily goals. This tactic enables them to focus on what is most important in the day ahead, better equipping them to chip away at the big number with a lot less stress.


How do you pitch Sprout Social to top-flight sales candidates?

My team at Sprout Social focuses on qualifying inbound leads and scheduling meetings for account executives, which means I’m often hiring sellers who are early on in their careers. With this in mind, I find it helpful to focus on one piece of the sales process that they can expect to truly master if they join Sprout.

I also highlight the incredible perks Sprout offers, such as an undefined PTO policy, unlimited snacks and beverages, and free workout classes twice a week. The best recruits typically are those who show curiosity in how they can grow, learn and hone their sales skills to advance their careers. For them, I emphasize our continuous opportunities for development through lunch and learns, one-on-one meetings with managers and more structured company-wide trainings.


dialogtech chicago tech company
image via dialogtech

DialogTech’s call analytics tools help companies get more customers on the phone and customize those calls to the caller’s exact needs. Matt Forcey, the company’s senior vice president of sales, said the key to succeeding in sales is to prepare better than the competition.


What is your secret sales weapon?  

Sales remains a competitive sport. Like in any sport, the professionals who not only work smarter but also work harder than their peers and their competition exponentially increase their chances of success. That sounds like a simple recipe, but it’s amazing how many of our peers in sales roles will rely on the product or the marketing message to do their job for them.

We win deals by being more prepared for the engagement than the competition, period. Be prepared to ask the hard questions, be prepared to be a guide and a facilitator, be prepared to align and build consensus, and be prepared to add value at every step.


How do you pitch DialogTech to top-flight sales candidates?

DialogTech provides a stable, resource-rich environment where professional salespeople succeed and thrive in an atmosphere of respect and collaboration. And our market-leading SaaS platform, leveraging cutting-edge AI and machine learning technologies, adds significant value to thousands of corporate marketers and agencies every day.


g2 crowd chicago tech company
image via g2 crowd

An online provider of reviews for business-to-business software and services, G2 Crowd helps companies find the tools they need to succeed. Founded in 2012, the company has gathered more than 340,000 reviews to date. For Andrew Stapleton, VP of customer success, the best way to succeed in the business is to take serious stock ahead of negotiations to ensure that the deal he reaches is one that will work for everyone.


What is your secret sales weapon?

Disempower yourself. Pre-determine how far you can go when your sale reaches the negotiation phase. Track everything your prospect could want and know what you can give ahead of time.


How do you pitch G2 Crowd to top-flight sales candidates?

You will learn a lot about how to sell from your work, as well as the products you’re pitching. G2 Crowd’s products solve problems across the spectrum of marketing and sales. Selling the tools that help sell other company’s products is a significant accomplishment. And our killer sales leaders and salespeople have become awesome professional mentors for one another, as well as their customers.


devbridge chicago tech company
image via devbridge

A tech consultancy that specializes in building custom software, DevBridge works with some of the world’s biggest companies. Adam Rusciolelli, who is the company’s VP of business development, said building successful partnerships depends on being transparent about exactly where his company’s expertise lies.


What is your secret sales weapon?

You must build trust quickly. Transparency and honesty are powerful tools to accelerate this. At Devbridge we are laser-focused on defining, designing, and delivering custom software that solve complex problems for large organizations. We let our prospects know where it makes sense to use our services and where it may not. This is a refreshing approach for many and builds trust that ultimately forms long-term relationships.


How do you pitch DevBridge to top-flight sales candidates?

We have a top-tier team known in the industry for over-delivering while solving big problems for organizations such as John Deere, Fitch Ratings and Grainger. Really believing in the teams behind the products we build makes selling our services incredibly exciting and rewarding.


narrative science chicago tech company
image via narrative science

With its AI-powered natural language generation technology, Narrative Science turns data sets into plain-English text. One of the company’s most successful sales strategies, said Matt Bramson, VP of sales, has been its formal entrance interviews with new clients, which ensure that everyone is on the same page about shared goals.


What is your secret sales weapon?

Shortly after we agree to enter into a partnership with a client, we organize an “entrance interview.” Imagine the opposite of an “exit interview.” We’re really able to understand why they chose to work with us and how they intend to capture value through the partnership. We then use these quotes to publish an internal press release, which ultimately rallies the entire organization around our clients. After all, everyone is in sales.


How do you pitch Narrative Science to top-flight sales candidates?

We believe that one single person shouldn't be charged with recruiting top-flight talent. It’s a team effort, so let me emphasize the "we." First, we need to understand what their motivators are. What are they passionate about? How do they measure themselves? What is their competitive outlet? Once there is alignment, we design a framework whereby we can help one another achieve our goals. Said differently, do they want a seat on the rocket ship?


lotlinx chicago tech company
image via lotlinx

LotLinx makes digital marketing tools that let car dealers target customers with ads for specific cars on their lots. This allows dealers to serve up relevant ads and move hard-to-sell vehicles more quickly. Pat Ward, who is the company’s chief revenue officer, believes sales success comes down to a number of key factors.


What is your secret sales weapon?

It’s really a combination of things. First, you have to recruit good people who fit with your culture and identify what makes certain people your “A players.” Through having a plan that everyone is familiar with, tracking progress and offering constructive feedback, you want to help other team members get there. When you do that, everyone wins. Also, never underestimate what a team can accomplish when they’re focused. I have seen 10 people with laser focus accomplish more in a month than 100 people without focus could.


How do you pitch LotLinx to top-flight sales candidates?

I’m not sure I’d call it a pitch, but I do share stories about the team. The most important thing, though, is believing in the product or services you’re offering. If you don’t believe in them, you need to find something else to do. But when you honestly believe in, and are passionate about, your company, it’s contagious.


urbanbound chicago tech company
image via urbanbound

UrbanBound’s relocation management software streamlines the process of moving for a job, making it easier for companies to recruit top talent from across the country. The platform helps employees deal with the logistics of moving, as well as getting to know their new home towns and neighborhoods. Chris Collins, UrbanBound’s VP of sales, attributes his team’s success to a willingness to improvise and play to its strengths.


What is your secret sales weapon?

We're primarily inside sales, so I cannot credit our insanely good looks as a secret weapon. That said, too often, salespeople rely on the messaging, collateral and processes that were bestowed upon them by their employer. They simply become sales robots. Our secret weapon is hiring sales professionals who play to their own unique strengths, internalize the value their company provides and then make the message their own.


How do you pitch UrbanBound to top-flight sales candidates?

UrbanBound represents the unique opportunity to sell something that never existed before, and as a result, our sales team is in the enviable position of having virtually limitless upside. Because we are nimble and growing, our team is highly collaborative and cross-functional. This is why we attract salespeople who want to make a larger impact than just selling. They want to contribute to the strategic direction of our business. Also, our volleyball team is pretty awesome.


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