Be honest, you didn't get into tech sales to make an average income.
If you're anything like me, you heard stories of elite reps making hundreds of thousands per year and you thought, why not me?
If you're getting this email, I'm going to assume you've already achieved the coveted six-figure W2 (no worries if you haven't yet; the skills needed to get to $100K+ aren't all that different than the ones it takes to get to $200K+ so keep reading...)
But, but, Jesse, $200K is a rookie number, I want to hit a $500K or even better a $1M W2. I live in [US Coastal City] and $200K is at the poverty line.
Patience young Jedi, I get it. $200K doesn't go as far as it used to, but I still see it as a major milestone in a tech selling career. If you live in a HCOL city, then you should definitely aim higher, but the behaviors required to clear $200K can also help you achieve uncapped earnings under the right circumstances.
Also note, my use of the word consistently. Many of the highest-earning reps I've spoken with over the years would gladly trade a single outsized earnings year (i.e. $500K, $700K, $1M etc.) for multiple years of consistent earnings. This makes it easier to stick to your financial plan, and manage your tax burden.
So, with all of that said, let's talk about the actions you can take to consistently earn multiple six figures, YoY, selling your wares... soft-wares.
#1 Strategic Selling
While not impossible, it's going to be much harder to clear $200K if you sell a transactional product to small businesses. This is basic math. If you sell a $12K/year SaaS product, you'll have to close a ton of deals, even if your commission % is 20%+ on the deal.
Enterprise AEs who sell a solution for $250K+/year at a 10% commission rate only need to sell about 4 deals per year to clear $200K since these commissions will typically be stacked on top of a $100K+ base salary (BTW $125K base is actually on the low-end for ENT AE comp).
Now imagine having a $150K/year base and selling deals in the high six and seven figures. This is the path.
How do you learn the art of strategic selling?
Simple, but not easy. You need to start by consistently selling deals in the five-figure annual range and prove you are ready for the Enterprise AE title. This may also require some strategic hops to make sure you are at a company with a solid product market fit (PMF) with a good comp plan. Territory and timing are also factors, but more on this later.
Key skillsets that will help here are: territory planning, research, multi-threading, exec peering, champion building and negotiation. There are a ton of resources for learning the above, but it is often best to learn by doing and working with leaders, peers and coaches who can help you develop these skills on a 1:1 basis.
#2 Executive Presence
If you want to close bigger, more strategic deals, you will need to learn how to think and act like an executive. This is often referred to as executive presence. Your ability to analyze, summarize, present and map back to business value will be critical for closing deals above $250K/year. Typically companies aren't going to invest that kind of budget without an exec-level sponsor overseeing the project. You'll need to learn how to work with execs (internally and externally) in order to win deals at this level.
How do you develop executive presence?
Spend time with execs. Make a point to connect with the decision makers in your deals. Practice being brief, dress for success, always bring a perspective and be intellectually curious (practice asking good questions). I always kick-off exec convos with a recap and summary of what we're trying to do, what's done and what needs to be done.
#3 Operations
To perform at a high level such that you can close larger deals and earn the commissions needed to clear $200K+ you'll need to learn how to be an operator. To me, this means building operating systems that will support your ability to scale your pipeline, deal management, discovery and paperwork.
How does one become an operator?
Start documenting your operating process, take good notes, come up with a plan for how to stay on top of deals while also spending time building pipeline doing research and managing the steps needed to get deals done. I guarantee your company has a lot of great resources for this already. Go find those resources while also building out your own. The highest earning reps are operators.
#4 Team Building & Delegation
I'm not talking about happy hours, pizza parties and ping pong games. High earning reps know that the biggest deals in the industry don't happen from one person's sales efforts. This is a team sport and winning the big deals that will unlock big earnings will come from your ability to build relationships with your internal team and assign or delegate tasks to the specialists within your company.
How can you improve here?
There are thousands of great books on management and organizational effectiveness. Start there. Spend time setting expectations with your teammates and peers. Ask for help and be proactive. You are the "quarterback" and you need to call the plays that will help you and your team win.
#5 Luck
I know, I know luck is not a skill, but the reality is a lot of your success and results will happen because of good luck. Inheriting a great region, account or active deal will go a long way toward earning multiple six figures in tech sales.
So, how can you manufacture luck?
Doing your due diligence i.e., joining the right company and team, consistently doing the revenue generating activities every day even when you don't feel like it. Making connections and nurturing professional relationships are all ways you can make luck. Practice keeping an eye out for opportunities (career and deal opportunities).
It's also important to maintain an abundance mindset, which is a skill. Developing all of the above skills will greatly improve your chances of getting lucky and signing the large deals that will consistently take you over the $200K W2 mark.
Final Thoughts
There are many skills to master on the journey to financial success in your tech sales career. The ones I've shared above are just the beginning.
Stay the course and aim for consistency and before you know it, you'll be making life changing money and funding the lifestyle of your dreams.
Thanks for following along and best of luck on achieving your earnings goals!
-Jesse