Career change

How to Navigate a Career Change in Enterprise Sales

It’s a great time to be in enterprise sales. Many industries—including SaaS products, cybersecurity, and healthcare—are poised for growth. Companies in these industries will thus need skilled salespeople to work on enterprise sales.

So if you want to enter enterprise sales, there are many opportunities available to you. The same is true for professionals who are already in enterprise sales, but want to enter a new industry or role.

Here are seven steps you can take to get started on your career change.

1. Take stock of what you want from a career.

The enterprise sales landscape is rife with opportunities. That’s great—but it also means that it can be more difficult to hone in on the right career path.

Before diving into job ads, it’s important to look at the big picture. Think about what you want from a career. What really makes you excited about sales? What do you want your professional life to look like?

Consider your skill profile. What skills do you currently have, and what would you like to learn going forward? It’s totally okay if you want to try something new, but you need to be honest with yourself about what you need to do.

2. Research the current enterprise sales landscape.

Enterprise sales is changing rapidly. Before making any major decisions, it’s helpful to look at what roles are available and how different roles fit into the larger business ecosystem.

The structure of enterprise sales teams can vary quite a bit between companies, even in the same industry. Even a cursory glance at job sites such as Glassdoor reveals that there are many different job titles for similar positions. Despite this variety, however, most enterprise sales roles are more heavily weighted towards one part of the customer journey: pre-sales, sales, or customer success.

To really get a feel for how different teams are structured in this regard, research a variety of companies. If possible, you might even conduct informational interviews with enterprise sales professionals across roles. If you’re new to enterprise sales, keep an open mind during your initial research. But as you learn more about different roles and industries, start thinking about what’s most exciting to you.

3. Identify long-term and short-term goals.

Once you’ve gathered information about different enterprise sales roles, it’s time to articulate your goals. What would you like to be doing within the next six months? In three years? Five years? Ten years? Be as specific as you possibly can.

Looking at other enterprise sales professionals’ career trajectories can be helpful for envisioning what’s possible for you. But keep in mind that everyone’s path in sales is different, and there is no single path to success.

4. Invest in your enterprise sales education.

Enterprise sales is a complex, constantly changing field. To succeed, it helps to arm yourself with as much information as possible. Even if you already have some enterprise sales experience, continued learning and skill development will only help your career.

Here are some ways to get started:

  • Read books about enterprise sales, selling techniques, and general business development.
  • Follow enterprise sales experts on social media. If they have blogs or podcasts, read and listen to them.
  • Join a local meetup group of enterprise sales professionals. This is also a great way to network.
  • If you can, attend an enterprise sales conference or training course. While this is by no means absolutely necessary, some people find it helpful for immersing themselves in enterprise sales.

5. Find mentors who can teach you the ropes.

Mentorship is critical for sales professionals. Make an effort to find a mentor—or, ideally, more than one—who can provide you with career guidance.

To find a mentor, try these tactics:

  • Search your professional network, including both past and current colleagues. Is there anyone who might be able to serve as a mentor? You might also ask trusted colleagues if they have any suggestions.
  • Tap your social network. Are you connected to anyone in enterprise sales?
  • Attend meetings and conferences for enterprise sales professionals. While you shouldn’t simply approach people asking for mentorship, be on the lookout for potential mentorship candidates. If you put in effort and navigate the situation deftly, you might find someone willing to provide mentorship.
  • Demonstrate your value in the workplace and give back to others. If you demonstrate an ability to reciprocate, potential mentors are more likely to invest time and energy in you.

Don’t be discouraged if you’re unable to find one person who is your formally designated mentor. Most successful enterprise sales professionals rely on an entire network of people.

6. Evaluate whether the best path forward for you lies in your current organization, or in a different organization.

Now that you know your goals, it’s time to make some tough decisions. You need to assess whether you can grow in enterprise sales at your current organization, or whether you will need to find a new position.

Some questions to consider:

  • Does the enterprise sales role I want exist within my organization?
  • Are the people I’m working with able to help me grow and develop new skills?
  • What opportunities for advancement exist within my organization?

It’s not necessary for you to feel like you want to stay with your current organization forever. But if you don’t think your organization offers opportunities for you to get on the right path towards your new career goals, it’s time to leave.

If you feel comfortable, talk about your career aspirations with a supervisor or someone else at your organization. They may be able to identify potential opportunities you don’t know about.

7. Create a game plan for your career switch.

Once you know your goals, make a step-by-step plan that will help you get there. Most of the steps should be things that are mostly within your control. Refer to the game plan periodically, and make changes as needed.

Your career probably won’t go exactly according to plan. But creating one is critical for your ultimate success.

James Meincke

James is the Head of Marketing @ Demodesk, the intelligent meeting platform for remote sales. Previously he was the Director of Marketing at CloserIQ.