The Story of Sales: How Skills and Learning Make for Successful Sales Reps

The sales rep role is as old as time, but one thing has remained the same — skills and the right mindset for the job. How Convoy and ComplYant are setting, and reaching, a high bar for their reps.

Written by Anderson Chen
Published on Dec. 07, 2022
The Story of Sales: How Skills and Learning Make for Successful Sales Reps
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Although the primordial form of the salesperson has long existed (as a peddler of wares and merchant networks of bygone eras), an organized salesforce of the modern corporation was a uniquely American invention. 

According to Walter Friedman, author of Birth of a Salesman, the manufacturing machinery that powered America atop the global stage in the late 19th century necessitated a stable network of salespeople to drive demand for products. And so, the modern sales rep was created. 

Today, the system of using a dedicated sales team to market products has remained consistent in its core functions. What’s changed, however, is the staggering number of channels that companies can now leverage, the tech available to reps to fine-tune efficiency and the products they now hawk via Zoom and email.

For companies like freight technology firm Convoy and sales engagement platform Outreach, sales departments must hold customer relationships to a high standard, honoring a dedication to the craft and skills for developing those relationships that transfers across time and tools. 

“Finding ways for Convoy and its customers to innovate together is the key to building lasting customer relationships that create value,” said Paige Roncke, Convoy’s director of sales enablement. 

On the recruiting side, the importance of sales reps and their enduring role in businesses have made it so successful teams now demand certain skill sets when looking to bolster their ranks. Cassie Pless, Outreach’s senior director of commercial sales, sees the quality of questions candidates ask as a good litmus test for their sales abilities. “An interview is all about mutual fit — show me you did your research and aren’t afraid to ask the hard questions,” she said. “This demonstrates how you’d be in a sales process.”

In modern society’s environment of constant change and innovation, certain sales traits transcend the commotion. Built In Seattle sat down with Roncke and Pless to see how they’ve maintained a high standard for the timeless job today.  

 

Paige Roncke
Director, Sales Enablement • Convoy

Convoy is a digital freight network that uses machine learning and automation to help the trucking industry — along with its associated shipper and carrier marketplace — reduce its carbon load and gain tech-powered efficiency. 

 

What is the number one skill you think new hires need to be successful on your team?

Convoy is focused on developing award-winning technology that enables our customers to more efficiently drive their business. The sales team is a key component to that endeavor; it has the onus to listen to Convoy’s customers and uncover problems to create opportunities for growth. In order to manage these opportunities, a new hire on the sales team is expected to fully embody our core values with drive and ingenuity. 

Seizing an opportunity to talk to customers and internal partners is a celebrated behavior amongst the Convoy leadership team and is one of the benefits of working for a startup of our size. Uncovering unique challenges within a customer’s business creates a platform for our sellers to collaborate with partner teams and drive results. Sellers have the opportunity to influence internal partners to think critically, innovate and create real value for their customers — and for their careers.

Seizing an opportunity to talk to customers and internal partners is a celebrated behavior and is one of the benefits of working for a startup of our size.”

 

How can sales candidates demonstrate that skill in a job interview?

Sales candidates interviewing at Convoy are asked to demonstrate their proficiency in sales skills, quota achievement and customer problem solving. Demonstrating by-the-numbers quota fulfillment is a necessary step in furthering an application. Highlighting sales skills through delivered artifacts is also a great avenue to demonstrate proficiency.

Sales candidates can stand apart by showing clear outcomes from solving customer problems. They should be able to clearly outline the problem, how the problem was identified and the proposed solution, as well as prove the successful outcome with data.

Candidates should lean into sharing specifics from past roles, like percentage of quota achievement, opportunities closed, deal size and new logos landed. These metrics are concrete insights to highlight during or before the interview process. Tailoring answers to show output instead of just inputs will set candidates apart.

Candidates should also demonstrate passion for their work, independent drive and enthusiasm to dive deep into problem sets. Showcasing past project work and customer testimonials will bolster such results.
 

What kind of training do you offer newly hired sales team members to set them up for success?

At Convoy we invest in our employees and their professional growth. In order to ensure a new hire’s success, the company offers a rich suite of learning and development opportunities in a variety of mediums that best suit the learner. Convoy’s learning and development paths are enriched by e-learning, cross functional shadow programs, individual hands-on coaching with expert trainers and group role-play sessions led by industry experts. Each track in the onboarding process is built to ensure new hires deeply understand goals, drivers to those goals and the ways in which customers derive value in our services.

Beyond onboarding, the sales training team will continue to build upon an employee’s personal and professional success by offering weekly, monthly and quarterly training tracks. These focus on ensuring sales members hit their quota and react to market shifts. Professional development certifications are also available to qualifying members of the sales team to invest in their long-term development and upskilling. Quarterly leadership training programs are offered to members of the team that consistently demonstrate Convoy’s core values.

 

 

Cassie Pless
Senior Director, Commercial Sales • Outreach

Outreach is a sales engagement platform that aims to make sales reps more productive through machine learning for automation and touchpoint prioritization, driving better customer engagement.

 

What is the number one skill you think new hires need to be successful on your team?

Curiosity. New hires that are naturally curious will quickly ramp up on the personas they are selling to, the problems they are solving for those customers and how to best demonstrate that value.

 

How can sales candidates demonstrate that skill in a job interview?

Bring good questions. Instead of asking, “Why do you like working at this company?” opt for, “I saw you just launched this product. Why are you winning? Why are you losing? How are you enabling your reps to win?” It shows your prep, curiosity and ability to ask the challenging questions.

Bring good questions [to the job interview]. It shows your prep, curiosity and ability to ask the challenging questions.” 

 

What kind of training do you offer newly hired sales team members to set them up for success?

We focus on active enablement and coaching. We have seasoned reps that overlay our new reps to ensure that we’re asking the right questions, getting to the right buyers and advancing deals in the right way.

 

Responses have been edited for length and clarity. Images provided by companies and Shutterstock.

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