• Before a company hires a new salesperson, it’s essential to have processes in place that will help the new employee succeed, which starts with finding a manager ready to invest in their growth.
  • Competitiveness, coachability, and location are the vital ingredients of a good salesperson. Whether you’re looking for a new job or trying to succeed in an active role, make sure you’re helping yourself thrive. 
  • Don’t expect monotony. In sales, different companies, roles, and locations will have different feelings and expectations. Be sure to treat application snags and sales problems like the unique challenges they are.

A good sales team is a thing of beauty.

Development reps scrounge for leads, using wiles and tenacity to find likely buyers. They qualify the ones they find and turn strangers into potential customers. 

Then there are the account executives: experienced, skilled, and always ready to move in for the close.

Whether you consider this relationship a one-two punch or a happy partnership, it takes work to get there. A great sales team is less like a family and more like a well-oiled machine, with each person thriving in their individual role to propel the whole group forward.

On an episode of the 0 to 5 Million podcast, Shawn Finder and Ollie Whitfield answered popular questions from prospective and up-and-coming salespeople to help them envision how to reach sales success.

Whether you’re a salesperson or an executive looking to put together your all-star sales lineup, you almost certainly hope to be part of a thriving team — here’s how to start. 

The 2 Ts of sales: tenacity and talent

Experience isn’t the only qualification that potential employers look for when it comes to hiring for sales roles.

Everyone who’s done any sort of cold calling knows that rejection might be lurking around any corner. A good salesperson is used to hearing the word “no” — but they’re always ready to learn from it and always primed to tackle sales obstacles as soon as they arise.

sales questions

If you want a sales job, you have to show that you’re ready to be tenacious. Hiring teams are looking for someone who won’t give up and who will respond well to constructive coaching. “If you’re not going to be able to get used to rejection, you will not be good in sales,” Shawn says.

This mindset serves both candidates and employers. The whole team grows when a salesperson wants to work hard to improve. A competitive, tenacious applicant can do more good than an experienced rep who is less hungry.

“If you’re looking to start a sales team, don’t always just pick the person that’s worked at IBM for three years,” Shawn advises. “Look for somebody that you think is talented but also coachable and that you can grow with.”

As a candidate, you should look for sales managers who will invest in your growth. A well-established sales team will be able to train you and help you grow toward your ambitions. Avoid companies without sales processes or adequate tech stacks — they aren’t set up to turn your effort into experience and expertise.

Face your own sales problems, find your own solutions

In a sales role, taking a step back to reevaluate can bring a heavy stigma. The sales world is a go, go, go culture, with quotas that need reaching and hefty performance bonuses for the high achievers. So when problems arise, the pressure to keep pushing forward and attempting to simply outwork the problem may feel overwhelming.

But noticing, diagnosing, and responding to those problems in creative ways can lead to newfound success, especially when you find solutions unique to your own personality and situation.

Unsatisfied in a “better” job

Ollie and Shawn got a question from an account executive (AE) who regretted transitioning away from his sales development representative (SDR) role. The salesperson makes more money now but is struggling to hit quota and feels unsatisfied in the new position.

For this AE, it’s time for a reckoning. 

  • Can they stomach the challenges of the AE role, but the sales just aren’t coming? 
  • Should they look for a new job altogether? 
  • Could there be a way to sort out the problem internally by speaking with a manager and suggesting a switch back to SDR or to a hybrid SDR and AE role? 

Whatever the solution, it’s important for this rep to determine their best interests and act on those.

“There’s no shame in [it] — if you are just a great SDR, go be that,” Ollie says. “There’s shame in carrying on and getting fired in a year’s time because you didn’t pull the trigger on knowing what to do.”

Whatever problem you’re facing, thoughtful analysis and a bias toward taking action are good places to start. 

Geographic disadvantage

An AE at a software-as-a-service (SaaS) platform working in the center of the U.S. noticed they weren’t closing as many sales as fellow representatives on the East and West Coasts. They churned through 200 to 300 cold calls a day and gave good product demos, but buyers simply weren’t biting.

sales questions

Ollie and Shawn’s advice? Move. The salesperson is clearly a capable caller and demonstrator, but their territory isn’t serving their abilities. They were right to attune to the experiences of fellow representatives in other regions and would benefit from a change of scenery.

For managers, a sales team member who seems out of the loop should get specific care and encouragement — some tailor-made way for them to feel seen. For instance, if an employee is vegetarian and you’re sending out holiday gift cards, skip the steakhouse.

Intentional and individual problem-solving can keep salespeople thriving, especially if problems at work start to overshadow the job itself.

Putting in the time for sales success

These days, it seems like everyone wants to move fast and skip rungs on the career ladder. But the early stages can hold valuable learning opportunities to help you build true sales success.

Cold calling, emailing, and messaging can feel repetitive. Though not always enjoyable at the moment, they produce consistent results over time and make a huge impact. Then, your days of talking to customers and working with businesses can pay off in spades later in your career.

“As a manager, you have to be able to coach, you have to be a leader, you have to train, you have to mentor, you have to understand what your team is doing,” Shawn explains. “The only way to do it is if you’ve done it before.”

If you’re new to sales, that might mean finding a telemarketing job to work on your pitch style. If you’re getting bored in an early role, start looking for ways that you’d teach a new employee to do your work. 

If you keep putting in the time, you might just get to hire your replacement.

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