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Hiring SDRs: How to Hire a World-Class Outbound Sales Team

At Chili Piper, our sales development representatives are absolutely kick-ass.

We have the world’s leading team of SDRs anywhere among any organization in any vertical. 

Yeah, I’m biased. But in case you think I’m being hyperbolic, the numbers don’t lie:

  • In one month, one SDR was responsible for sourcing 32 completely cold, outbound meetings
  • In 2020, we promoted 5 quota-crushing SDRs to AE, AM, and ENT SDR positions
  • The SDR team increased Closed Won Revenue in 2020 from 2019 by 711%

The obvious question is, how?

How did we build a fantastic SDR team that achieves record-smashing success? 

How, especially, in the midst of a global pandemic when a lot of companies were in hiring freezes (at best) or letting go a third of their team?

And how did our team not lose our minds in the process? 

This is our tell-all — how we built a world-class outbound sales team. We’ve held nothing back.

Here is our exact process, email assessments, and even the wording of our job application. 

But first, a quick introduction. 

Hi, I’m Matthew Roberts. Here’s my background at Chili Piper. 

I’m the Director of Sales Development at Chili Piper, the company where I’ve spent a fantastic one year and 10 months. 

I have always been grateful for my eclectic background, with a vast array of industries, like hospitality, film production, tech sales, marketing, entrepreneurship-focused on mental health, and eventually, back to tech sales.

The journey is what I love more than anything. I can honestly say I’m happy doing what I do. 

Interestingly enough I shared my resume with our Head of Talent who said, “job hoppiness” in sales roles usually means that “they can’t hack it or that they don’t actually enjoy the work.”

After a good laugh, we discussed how often the most successful people have the largest range of experience and often have meandering paths to where they are. 

That really resonated with me. Varied experience means you’ve navigated different situations.

To me, the one thing that bonds all of my past positions together is working with people. 

I was attracted to Chili Piper because of three primary features:

  1. An extremely valuable product
  2. A fantastic company culture, and 
  3. Leadership that I wanted to learn under.

I started as an SDR because I figured that was my best chance at getting in and learning from the ground up. The company was sitting at around 25 people. 

Once I had proven myself and seen success as an SDR,  we talked about making the leap to account executive. But I realized I truly enjoyed helping people on our own team succeed. 

Since I wasn’t certain of which position would be best for me next, I naturally felt myself shifting into the SDR Manager position, and most recently being promoted to director.

The best advice I received while moving in this direction was from fellow colleague Michael Tuso. He said, “Do the position you want next before you have the title, make it obvious that you deserve a promotion.” 

Those valuable words kicked me into another gear. I quickly found myself getting involved in everything I could. From creating internal and fun initiatives to promote our amazing culture, getting involved in the interviewing and hiring process for the SDR team, onboarding new reps, and eventually, acting as an SDR Manager before the title was on my LinkedIn.

I still believe there is no better way than getting the job you want, than doing it before it’s yours.

That’s why I want to share the things that I learned about developing an SDR team that blew my mind and catapulted Chili Piper to such dizzying heights of success. 

This is the process we use for hiring the perfect SDRs every time 

The hiring process is the most important step in developing a kick-ass SDR team. 

Keep in mind, Chili Piper is 100 percent remote, so I don’t interview in person. 

A few hiring principles quickly emerged as I began onboarding new SDRs for our team. 

General Hiring Criteria

  1. Make it difficult. A difficult hiring process doesn’t mean it’s unkind. It simply means that it’s stringent. You get to decide who a qualified applicant is, and that usually means raising the bar in terms of experience and knowledge. 
  2. Be picky. We average 250 applicants for every open SDR position. There’s no way I’m conducting 250 interviews, so I’ve developed quick-and-dirty heuristics for who makes the cut to the next phase and who doesn’t. This is a gut-check process that takes mere seconds and is nearly impossible to codify, but I’ll give some pointers in the next section. 
  3. Add in assessments to assess their “grind” or “grit” from afar. Candidates who want the position will take the time to complete tests and create sample projects. Don’t be afraid to add in qualifying assessments to screen tire-kickers from serious candidates. 
  4. Select candidates who put in the extra work. “Extra effort” is easy to notice. They’re the ones who go above and beyond; they send you an extra email, follow up after a call, and do more than expected. The ones who are doing that in the hiring process will likely do that once they secure the position.

Chili Piper’s Standard Job Posting

Everything begins, of course, with our job posting for SDRs, posted on the standard job boards such as Glassdoor, WeWorkRemotely, LinkedIn, etc. 

This obviously brings in a flood of candidates — equal parts qualified and unqualified.

I spend hours sifting through resumes to get a clear sense of which applicants possess the relevant experience and skillset. 

How We Developed a Remote-First Hiring Process

One of the best things I was able to do is get involved in the hiring process early on for the SDR team.

By getting involved early, I was able to make selections, build observations, and grow a hiring muscle that trained me to better screen the dozens of applicants with whom I would eventually speak.

We quickly developed a process that I truly believe in and one that is able to eliminate most of the worries that leaders have when hiring remotely.

There’s this dreadful myth that interviews are a draining and onerous process for job candidates. This shouldn’t be the case.

Candidates are just as much in the driver’s seat as the hiring manager. They can and should qualify the opportunity, culture, and position based on their own preferences, work style, and skills. 

I love it when candidates tell me that the hiring process at Chili Piper was one of the most rewarding, fun, and memorable of their experiences. That kind of introduction to the company makes a great impression on incoming employees.

Keep in mind: Chili Piper has been remote from day one. We have 90 team members and no central office. Our team lives in 18 countries and 64 cities all across the globe. 

Hiring remotely is what we do. There’s no other option. 

Chili Piper’s SDR Interview Process

We have a five-step interview process, detailed below. 

1. Video Application

First, we ask candidates to record a short video and answer a few questions. 

This isn’t a ground-breaking interview technique. But it is powerful. 

Instantly, you get a sense of whether or not the SDR has the presence and personality to make it in a sales role.

Plus, the candidate has a chance to exhibit some creativity. You get to see who stands out from the crowd. There’s a lot you can do on a two-minute video screen — you’d be surprised.

2. First Face-to-Face Interview with the SDR Manager (That’s Me)

This is the initial live interview, and it happens on Zoom. 

By this point, I’ve seen the video, I know their resume.

Now, I want to get to know them personally and who they are as a human being. 

Learn what motivates them, what inspires them, what are they looking for in not only a career but in life. 

I believe the more you are in the interview, the better off things will be in the process. 

Interviewing is about a fit on both sides, not just trying to impress someone, or on the hiring size and selling the company to someone who isn’t a good fit. 

Make sure both parties are excited about this opportunity. 

Here are some of the features I’m looking for during that first crucial face-to-face interview. 

  • The candidate knows what they want in their career.
  • They’re sharp. 
  • They are flexible, fun, and easy to talk with. Conversational twists and turns don’t throw them off. They roll with it. 
  • They are confident.
  • They are friendly. 
  • They are curious. 
  • They are articulate. 
  • They are thoughtful — not too deep that they seem creepy, but not so casual that they seem superficial
  • They have the ability to ask meaningful questions. The questions they ask are, in my experience, more important than their responses to my questions. 

Candidates that pass muster on this evaluation are greenlighted to the next phase. 

3.  Email Assessment

The substance of our email assessment is less about their literal responses and more about the effort they put into it. 

Here is the actual email assessment I send to every SDR candidate who passes the second phase of the process: 

Hi NAME,
Thank you for your time! As mentioned, the next step in our process is a prospecting/cold email assessment. Please do enough research on Chili Piper to make this relevant.
Look into these 4 companies to find which one would be the best fit for Chili Piper’s concierge product: AdidasAmazonZoom, and Wingman
Identify 2 potential prospects or decision-makers at the company of your choosing using any and all resources at your disposal (LinkedIn, Google, etc.)
Goal: Generate curiosity to initiate a response to see if Chili Piper could provide value.
Deliverable A: Provide which company was selected and why, as well as the list of both prospects (including their names & titles). 
Deliverable B: Craft a two-email cadence that you would send to earn the right to a conversation. 
If you have any questions, please let me know. When you’re done, submit your work to the Greenhouse link provided.
Good luck!
Matthew

I’ve found that email assessment responses can be put into two categories:

  1. Category 1: Fill this thing out. Send it in. 
  2. Category 2: I want to be a Piper, and I will give it my all to make this happen.

There is sometimes an 80 percent falloff at this point. As you can probably guess, a lot more candidates land in category 1 than category 2. 

The category two candidates — I want to be a Piper, and I will give it my all to make this happen — often provide awesome ideas that that may someday be put into practice. 

I collect the really good responses, shortlist those candidates, and send them on to the next phase of our interview process. 

4. Interview with Director of Revenue Performance

Michael Tuso, Chili Piper’s Director of Revenue Performance, is a living sales encyclopedia with the absolute best coaching skills and sales experience one could ask for. 

What Tuso is looking for essentially boils down to three things:

  1. The friendly, culture-fitting, confident person
  2. The person who has a knack for sales
  3. The person who can conduct great discovery and book a meeting

He’s not looking for someone who checks one or two of the boxes.

He’s looking for candidates who check all three. 

That’s what sales is — mindset, knowledge, and skill.

Once Tuso stamps his “approval” on a candidate, it’s on to the final boss. 

Office Space GIF by 20th Century Fox Home Entertainment

Interview with the CEO 

Lastly, they go to the CEO himself, Nicolas V. 

I love that our CEO is part of the process and still interviews with SDR candidates. He’s committed to doing so until Chili Piper’s 500th hire. This shows how involved Nicolas is with the everyday operations and every person at this company. 

His role in the interviewing process can be intimidating for a lot of people. That’s okay. In fact, that’s a good thing. 

When you keep an SDR on their toes, the job can be uncomfortable, confusing, stressful, scary, and that’s what makes it fun. 

There is no telling what direction the interview is going to take when you get in front of him.

In case you’re reading this article hoping to be hired at Chili Piper someday, how the final interview goes is anyone’s guess — including mine. 

My Conclusion: Our process works, but it has to be yours

Find out what works for you and make sure you have multiple steps in the process. Your process can and should evolve as you learn from your mistakes, experiences, and successes, but it needs to be repeatable.

Here are three key pieces of advice I can give you, based on my experience: 

  • Borrow best practices from a few different companies you look up to
  • Protect your calendar from those who may waste your time
  • Create assessments that reveal the skills for the position you’re looking to hire for

If you do all of this, you’re on the right track. And just like sales in general, you can tweak and A/B test different steps in order to optimize your hiring process.

Best of luck out there!