If you are the #1 or #2 ranked salesperson at your company, do often wonder, “could I be making more money somewhere else?” and “who are the companies that could offer me the right upside career opportunity?” What would it take to offset the risk of leaving your company where you are the top dog? Do you know when it’s time to leave, or when to jump at a great opportunity? How do you approach finding the absolute best opportunity?

At my company, we have spent the better half of the last 5 months talking to hundreds of high performing salespeople. Our goal? Trying to validate our theory that the right application of data will answer these questions and ultimately solve this problem. A large percentage of these salespeople were in Marketing Technology and Ad Technology, but we also spoke to a variety of SaaS salespeople, IT sales, pharmaceutical, financial services and even offline products and services salespeople.

Key Takeaways

Most of the salespeople we spoke to have been ranked #1 — #3 on their sales teams and confirmed that it is very difficult and time consuming to answer these questions themselves. Even though you want the answers — it clearly takes a lot of time and effort do a thorough job researching and meeting the right companies. Most top salespeople are busy closing deals, and have trouble finding the time to put in the work.

It’s not that high performers aren’t willing to put forth effort, your success proves you know how to work hard. It’s the fact that there is a higher opportunity cost for salespeople in trying to uncover the right data points about other companies and opportunities to help make an informed decision.

It doesn’t seem worth it to spend 3 to 4 hours per week thinking, researching, emailing and networking just to find out that most of the companies out there may not offer the right fit in terms of compensation, deal structure and sales environment to offset the risk of taking the jump. It seems easy to fall back into the day to day as that time can be applied to closing another deal at your current company, even if there are diminishing returns on your long term career upside.

5 Tips

Because for you time is literally money, here are the five tips that will help you maximize your time as you start to consider exploring what’s out there:

1) Think like an investor

Most VC’s out there like to invest in the right founders and also strategically choose a niche so they can be most efficient building their portfolio. Your networking time with other companies is you building your career portfolio. Make sure you choose to spend your time with the right people at the right companies.

2) Start at the top

While it may be tempting to respond to a recruiter’s email, you’ll probably need to start at the bottom and go through a “phone screen” first. Take the approach of only starting the process with a company if the VP of Sales or CRO is the first meeting. Since you are a high performer, you have earned the right to explore the business and find out if you can make an impact. It’s not worth your time to help someone match you against bullet points on a job description.

3) Play the long game

When you land a meeting with a VP of Sales or CRO, it’s the start of a relationship. If you don’t hear exactly what you want, don’t stop asking questions or showing interest. You already chose to investment your time, not all investments turn fruitful right away. This company or VP / CRO may not land your next job but it may help you land your first management opportunity down the road.

4) Be in discovery mode

As you know, the best salespeople love asking the right questions and are at their best in discovery mode. Come prepared to ask great questions, show your interest level and be a great listener. Regardless of whether or not you end up exploring the career opportunity, it is the perfect time to be in learning mode. What you take away could help you close a deal at your current company, give you perspective on a completely different opportunity or give you key market insight.

5) Be excellent at the little things.

Write thank you notes within 24 hours. Be courteous and kind. Offer to make some connections that may help — it’s fundamental to being a great networker. Set clear expectations for how you are thinking about your next career move, and if they change be communicative. The little things matter and are a live example of how you’ll treat clients if the person from the company you are meeting with were to hire you, they matter!

If you are willing to put in the time and effort to explore and reach out to the tens if not hundreds of companies out there there that need a high performer just like you, do so smartly. It may be a lot to think about at first, but if you are data driven and do one meeting or phone call per week with the right approach, it will pay off. Building your career network at your pace is the right way to go and will make what used to be a painful, reactive job search experience more proactive, fun and interesting.

If you’d like a free demo of the Upsider platform to learn how we are using data to help connect high performing salespeople and sales hiring teams, please visit our website: