Building an $11M a Year Business in Less Than 24 Months

Intended Audience: Quota carrying individuals, particularly in SaaS. Strategic Sellers?

Estimated Reading Time: 6 - 7 minutes

Highlights: For individual contributors who have large ARR (Annual Recurring Revenue) targets, here are some proven steps to successfully build an 8-figure+ annual book of business:

• Treat yourself like your own startup and your company as a venture capital firm who has a large stake in your success
• When you start out at your organization, say yes to every opportunity that comes your way, and then once you’ve established yourself, become more strategic with your time and efforts
• Nothing great is achieved alone, so it’s important to rally the organization behind your strategic pursuits
• Keep things interesting and fun by making selling a game
• Once you’ve established a baseline, setting and reaching goals becomes solving a math equation based on your own personal data

Build an ‘intraprenuerial’ mindset?

As salespeople, we sit in an interesting role inside our organizations. Once you’ve proven yourself as an individual contributor, you can gain tremendous levels of freedom, flexibility, respect and income. In many ways, these attributes are akin to successful entrepreneurs.

This is the way we need to operate!

As an intrapreneur, you have the ability to run a business inside a business. Salespeople have all of the headaches and risks of starting a business removed from our plates by our employers. Instead, we can focus solely on building our brand and growing our business.

Your dedication to your business needs to be a personal one, where you go all-in with your energy, focus and effort. Remember, it’s your reputation on the line, not just the company’s.?

It’s all about saying yes at the beginning and then no later

Before I started at LivePerson two years ago, step 1 was to ensure I didn’t burn any bridges with my former employer, and step 2 was all about building as many new bridges to future opportunities with strategic partners like Apple and IBM, who were partnered with my old company, but also the one I was joining.

By reaching out to my contacts in my network and embracing opportunity from every angle, literally my first day on the job put me in a position to actually sell into a large warm prospect. My contacts at Apple were able to set up a meeting with me on that first day at the NRF show that months later turned into one of our most talked about and exciting strategic account partnerships of the year.

Fast-forward to 2019, I had to be a lot more selective in where I focused my energy and time if I wanted to deliver my best work and land the biggest deals. Success didn’t come from saying yes to every single opportunity that came across my desk - that would have watered down my pipeline and pulled me in too many different directions. Instead, it was about a highly concentrated, more strategic focus on very specific accounts where I could truly be a partner vs a transactional salesperson.

I’ve seen many salespeople struggle by doing the opposite - they overthink things and endeavor to be too strategic when just starting out instead of just throwing themselves into the fire and learn by doing. Conversely, I see others who are more established spread themselves too thin because they think they have to hoard every lead and account possible rather than just passing them on to another rep who has more capacity.

?? Diamond tip: Trust in karma and sharpen your instincts!

Leverage the collective brain power of your organization

My mantra is “Nothing great is achieved alone!” This is especially true in strategic sales, particularly as individual contributors who don’t have dedicated employees working under us. You have to leave your ego at the door and realize there are folks who possess a lot more knowledge and experience than you at your organization.

As strategic sellers and good intrapreneurs, it is our primary role to rally the organization behind our efforts.?Partner with the best people in your company and put their talent on showcase in front of your prospects. Everyone benefits - you, your teammates and the client!

In another analogy, say sports, think of yourself like a quarterback or a playmaker, and get that great talent excited to want to play on your team.?It’s not about scoring every goal or taking every shot yourself, the G.O.A.T.s in sports knew/know when the right time to pass or get that crucial assist, and more importantly, make the other individual shine when the big game (deal) is on the line.

Make the process a game

Ok, let’s keep up with the sports theme, shall we??

When hunting the whales and the big strategic deals that snag the major headlines, it’s all about the long game. You have to realize there will be quiet stretches between deals, so in order to keep things fun and interesting, I’m a big believer in gamifying the process.

As a former soccer player, here’s the way I look at it: Salespeople, we're a lot like the professional athletes for our organizations. It’s not about just winning one game; it’s about showing up every week, putting in the effort (knowing that most of it won’t be recognized) and winning the season, winning every single trophy, multiple championships season after season, etc. Remember, we’re going after G.O.A.T. status here!

That means we have to eat properly, sleep well, put in intense work when it’s time to work, and put in serious recovery when it’s time to rest. I envision one day when health tracking is connected to a dynamic CRM where salespeople perform in different ways based on key metrics like rest, nutrition, variable heart rate, workload, target accounts, etc. You heard it here first! ??

Strong sales results are an outcome, not a pursuit. My pursuit is the score I keep on a daily, weekly, monthly, quarterly and annual basis. I use tools like Timeular and Pomodoro Technique to track how many focused efforts I completed in the day. I use Evo Planner for writing and planning, and then tracking a digital representation of my holistic “life score.” I use Whoop and Streaks to keep me on track with healthy habits. And of course, tools like The Sales Journal and The Sales House help map out the tactical side of sales success.

World-class athletes have every part of their schedule planned, diet calculated and training regime meticulously mapped out. As an aspiring world-class salesperson, why would we operate in any other way?

Obsess about the numbers and solve a math equation

If you are seeking to push your deals up a rung, say from six figure averages to seven figure averages, then you need to keep track of your numbers and then use that data in your strategic planning process.?

If my average deal size is X and I want it to by Y, what do I need to change...what activities do I need to focus on...what skills do I need to sharpen?

Here is a Personal Sales Stats sheet that I created which hone in on the most important metrics that are important to me. Feel free to make a copy and use this for yourself.

For me, the key metrics are understanding average deal size and hourly pay (income vs hours logged in my company’s HR system). Those two metrics define how I plan out my upcoming year- How do I increase my deal size? What does an hour of my time mean to my bottom line? Trust me, when this number becomes fully crystallized, you view time in a completely different manner and want to use it more wisely!

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If you like this, you'll want to unlock 7 Steps to 7 Figures, the exact system I used to go from earning $200K to $1M+ a year in SaaS sales without burning out.

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