6 Hard-Earned Lessons From a Top-Performing SDR's First 12 Months

Fresh out of college and looking to make my mark, I decided to join the tech startup world. I was excited to be offered a position at Veelo Inc., makers of a sales effectiveness software platform that helps companies provide personalized marketing content recommendations, coaching, and training for their reps.

I started as a Sales Development Rep (SDR).

Like most entry-level jobs, the SDR life is not glamorous. It’s also far from easy -- definitely not a job for everyone. I call the same prospects as hundreds of other SDRs from other companies, all with the objective of getting meetings with unbelievably busy vice presidents who run multi-million dollar organizations.

However, the SDR role is vital to the success of any growth company. And for me and many other SDRs, it’s a great place to start a career in sales because it affords the opportunity to fail fast and learn and grow at lightning speed. In just about a year, I’ve gone from a “green” college grad to our company’s top-performing SDR. I’ve learned a lot, made plenty of mistakes, and received coaching from some unexpected places -- and I wouldn’t trade any of it.

Here are six lessons I’ve learned in my first 12 months on the job.

1) Quality Beats Quantity in Prospecting

In the beginning, my strategy was simple: Contact as many people as possible. I reasoned that the more times I cast my line out, the more fish I would catch.

To a certain extent, it worked. I generated meetings. Unfortunately, they weren’t always meetings with qualified buyers in one of our target markets. And this wasn’t a great use of anyone’s time.

Over time, I got better at picking the right targets, experimented with different ways of reaching out, and ultimately, improved my results. During that process, I realized that improving the quality of my approach and only contacting good fit buyers is paramount to prospecting success.

During one of my fishing expeditions, I came across Pete Caputa, VP of Sales at HubSpot. To my surprise, Pete responded to me and we ended up having a number of email exchanges, but not about buying my product. Instead, Pete offered mentorship and advice. I shared my approach and scripts and he came back with advice and suggested blog posts and books to help me refine my outreach strategy.  

Of course, I’ve received mentorship and training at our own company too (after all, the value proposition of our product is to improve salespeople’s effectiveness). Without this help, I imagine I’d still be trying to hit my goals through a brute force quantity over quality approach to prospecting.

Once I adopted the right mindset, how exactly did I improve the quality of my approach? Keep reading.

2) Research Your Prospect Before Reaching Out

The first thing I began doing to improve my connect rate was researching my prospects. Think of pre-call research like doing your homework in college. Just like it’s hard to pass an exam without doing your coursework throughout the semester, it’s really difficult to get a response from a busy person without learning a few things about them first.

Once you do your research, make this fact abundantly clear in your prospecting messages. Don’t be a robot and send the same uncustomized message to each and every single buyer. Buyers recognize when they get generic subject lines and email templates -- and this makes it easy for them to ignore you. After all, you didn’t put in the work to get to know them, so why should they get to know you?

Instead, improve your chances of making a personal connection and getting a response by personalizing your email. Yes, it takes longer, but I have found that I can get a response from almost anyone by sticking to this rule. Here are a few steps I follow to make my research process as efficient as possible:

1. Check your prospect’s LinkedIn profile.
2. Follow any links to additional information about them.
3. Find something they are passionate about.

Here’s an example of what can happen when you implement this process. When I reached out to Pete, he eventually pointed me towards Andrew Quinn as the right contact. Following the instructions in an article Pete sent me about doing prospecting research, I went over to Andrew’s LinkedIn page. There I learned that his nickname is the “Sales Doctor,” and discovered that he performs in an '80s cover rock band called Wildside.

The email I sent him using this information:

 

Customizing my emails to this extent has helped me improve my connect rate significantly.

3) Do Something to Really Stand Out

At Veelo, we primarily sell to Sales VPs at mid-market companies. Given the boom in sales technology, these people are inundated with messages from hundreds of SDRs from different companies every single day. To get through to these busy prospects, I realized I needed to really stand out.

What makes you stand out from the pack? To catch my prospects’ attention I use (tasteful) humor, vary my attempts between phone, email, Twitter, and LinkedIn, and most of all, spend even more time on my research. When I can, I combine all three tactics.

For example, I watched a webinar presented by one of my target buyers as a way of researching her. In the recording, the Sales VP spoke about her favorite food spot in college called “Cosmos” and even mentioned the spicy ranch dressing the restaurant was known for.  

Here’s the first message I sent this VP:

 

4) Measure Results to Improve Over Time

Trial and error has been key to my development. Although I read a lot of sales advice, nothing beats trying things for myself and keeping tabs on what happens. I may think I’ve crafted the “golden email,” but until I test it, I have no idea if it will be effective. When a certain template works well, I use it again, and if it doesn’t, I toss it. In addition, I’m always tweaking my existing templates to make them shorter, more concise, and more compelling.

Below is one of my first emails, similar to what I originally sent to Pete:

 

This worked okay for me. But, through some testing, I realized that if I personalized the note and shortened it a bit, I got more responses.

Here’s a newer version that gets a far better response rate:  

  

5) Seek Out Mentors and Implement Their Advice

As a millennial fresh out of college, I’m supposed to have an entitlement mindset, according to the studies and the press. But I don’t. In sales especially, I realized I need to do more than just work hard to achieve my goals -- I have to constantly improve my skills too.

However, that doesn’t mean I have to do it alone. More than a few times, I’ve found that smart and successful people who I admire are willing to give me guidance. All I’ve had to do is ask, and show appreciation. In fact, more than one mentor has told me they appreciate the fact that I am so willing to implement their advice. As an example, once I told Pete that I’d be willing to share my results from what I’ve learned from him, he spent even more time helping me think about what I should try next.

6) Share What You Learn

As I write this article, I’m excited to pass along my new-found knowledge to other people. While I don’t have nearly as much experience as my mentors, I hope this post will help others just starting out in sales improve their results.

Many new SDRs and even some sales managers assume that volume and persistence is the to key being a successful SDR. Don’t get me wrong -- these things are important. But volume and persistence alone didn’t get me to the top of my class. By taking a creative and iterative approach, I’ve been able to make more meaningful connections.

I’d encourage you to critically think about what you’re doing now, get some feedback, and then try new approaches, measure how they work, and incorporate the stars into your routine. Through trial and error, I’ve crafted a unique sales approach that get responses. Extreme personalization helps me provoke smiles or even a laugh once in awhile -- which then earns me their attention and time.

For the past three months I have led the SDR team in meetings set, and for this month I’m on track to breaking the record for most meetings booked in a given month. My meetings are also turning into qualified opportunities with decision makers at a higher rate than those of my peers. But more important than crushing my goals is the fact that I’m helping more Sales VPs optimize their teams’ processes. And that’s a great feeling.

I hope this SDR who "started from the bottom" inspires some creativity in your prospecting. If you’re a sales leader and you want to know more about how these approaches or Veelo can help you improve your sales effectiveness, connect with me on LinkedIn or Twitter @DandersonDaniel. I’d appreciate the opportunity to share what I know and learn from you too.