How I Hit 100% of My Annual Quota in the First 6 Months of the Year

People shy away from sales because of the risk. It’s a profession where the highs are oh-so-high and the lows can take you to the depths of despair. If you are worried about making rent, a mortgage to pay or have a family to support, the risk to pursue a career in sales can be too great. With that said, it can also be one of the most rewarding careers. Your earning potential is often unlimited. The work you put in dictates the rewards you extract. Nothing is more satisfying than the high you get from realizing the fruits of your labor.

In June of this year, I hit a historic landmark in my career: achieving 100% of my annual quota in only six months. This doesn’t just happen by luck. Especially in a highly competitive SaaS environment where I sell a premium product into a market segment known for tight budgets. I made strategic investments in my process, mindset, and work ethic to do this. I leveraged every tool at my disposal. After reflecting on this achievement, I boiled down my learnings into a helpful formula that can improve the performance of sales leaders, individual contributors, and entrepreneurs working to get their product to market.

Leveraging the Technology Stack

Salespeople often joke about automation killing their profession. Will machines eventually take over? I don’t think so. You can’t program a computer to have a personality and EQ like mine. Still, there are amazing tools out there that can 10x the productivity of a salesperson.

I start with a sales automation tool like SalesLoft. In my opinion, SalesLoft and Outreach are the best out there. These tools are designed for SDRs (Sales Development Representatives) to source more opportunities, but I’ve hacked SalesLoft to help me close more deals.

The winning feature of a tool like SalesLoft is it’s ability to run a “cadence,” a structured series of emails and touch points that keep a prospect engaged. I have cadences built out for all kinds of scenarios that range from industry, to purchasing time frame, to individual areas of interest. Further, SalesLoft has features like “snippets” that allow me to paste together quick templates of helpful content for any follow up emails. It’s the perfect blend of automation and personalization. On top of this, my emails are tracked so I know exactly when my prospects are opening them.

The end result is that I can work a far larger pipeline than your average salesperson and have most of my follow up actions automated. By semi-automating much of this process (often, the most time consuming part of sales), I free up time to focus on more strategic areas of my job. As prospects become more engaged with my emails, I take them out of the cadence and revert to more personalized communication and “reminders” for next touch points.

I also use another sales enablement tool called Guru to rapidly find and share relevant content with prospects. Our team does a great job of keeping content fresh and updated. Not only can I use this to quickly find answers to questions my prospects have (speeding up my time to respond), I also use Guru’s document tracking feature to understand what content my prospects find most engaging. In short, I have a bunch of great content uploaded to Guru in PDFs. I can create a trackable link of that PDF and include in emails. While SalesLoft helps me understand when and how many times my prospects open my emails, Guru shows me exactly what content they found most engaging.

For example, I may get an alert that a prospect just opened a proposal I sent. I’ll immediately pick up the phone and call them. I’ll say something like, “I thought it might be helpful to walk through our pricing options.” This gives me the opportunity to walk them through the pricing, answer questions they have, and get valuable insights into what they are thinking about the purchase. The prospect likely finds this really helpful or thinks I’m a psychic.


To be a great salesperson, you also need to get behind a great product. Great products win and do part of the selling for you. If the product isn’t great, the salesperson often has to rely on hosing the customer to win the deal. That is simply unsustainable.

Fortunately for me, Greenhouse is an amazing product. Our customers love it and we have a great reputation in the marketplace.

So if the product is great, the salesperson must also be great at selling it. By this, I mean that they can’t just show “what” the product is, they have to show “why” it’s so great. This is value selling. When I do a demo or discuss anything about the product, I never just show the features. I’ve created stories for every part of the product. These stories demonstrate the “why” and get the customer to envision how their life, work, or company will be a whole lot better with this product.

Take the time to look at every winning feature of your product and create a story around it. Use rich examples of real (or imaginary)customers and how they benefited from that feature. Your demos and conversations will be much more compelling and the information will stick in your audience’s head.

This is especially important in the SaaS business where competing products quickly match each other in features. You need your customer to understand and remember how you do it better than the competition.


This realization was a fortunate byproduct of my sales leadership team’s slowness in assigning annual quotas this year. We run on a normal calendar year (January-December) and I didn’t find out my annual quota until late March.

For the first three months of the year, I joked that the quotas were going to be double what they were last year. This joke quickly started to sink in and I operated under this assumption. I envisioned myself hitting this doubled quota. I started operating differently. I built better processes into my work. I put in extra time with the deals that mattered. As the deals started rolling in, I picked up the pace.

If you can cement an image like that in your mind, little things will start to change in your effort and behavior. It’ll be slow at first but there is a snowball effect if you keep it up. So my advice to every salesperson out there is to take whatever your normal goal is and double it. BELIEVE that you can achieve this. Remind yourself every day that you are on the path to this achievement. Follow your natural intuitions on how you are going to accomplish your goal. You just might get there.


All of this culminates in what I call End of Funnel Efficiency. Marketing takes care of the beginning of the funnel, Sales takes care of the end. If you can apply marketing efficiency tactics to your sales procedures as I have, you end up with a much larger pool of achievable deals. Combine this with targeted value selling and your end of funnel gets even wider. Top it all off with the mindset that you will go above and beyond normal goals and you will be unstoppable!