After several wild and mostly wonderful years as a quota-carrying AE (Account Executive), I recently moved into an ADR (Account Development Representative) leadership role here at Skilljar, and it turns out that this critical and oft-misunderstood function has evolved considerably since I last prospected full time. After three months, here are my observations so far.


1. The ADR role is more business-critical than ever before: Skilljar is an enterprise SaaS platform, selling to innovative training and enablement teams across a wide spectrum of industries and segments. In this world, there are many, many technology providers competing for mindshare, and sending untrained reps to prospect into the c-suite simply doesn’t work. Today’s ADRs need the skills and enablement to have sophisticated, quick-pivot conversations about ways their solution can improve a buyer’s key business metrics. In short, the ADRs that deliver impact are great sales professionals who today own a portion of the pipeline, and could tomorrow grow to own the entire pipeline.
2. Cold-calling isn’t dead: Well, of course not, but I think there’s a more nuanced truth hiding behind the clickbait. Cold-calling is really, really hard, and current market dynamics have made it that much more difficult. Crisp, value-adding, tailored conversations are still the single best prospecting method in existence, but bad cold-calling is a great way to lose a chance at a prospect relationship. Just because it’s not easy doesn’t mean you shouldn’t do it. If anything, if you get this right, you can really stand out in the market and in your career!
3. Email for volume, social for familiarity, direct mail for surprise, dials make $: Related to #2, and if I might be allowed to break into pure tactical mode for a moment (which I am, since it’s my blog post): Executive buyers get a ton of email and more connection requests / in-mails than they can read. Rarely do they have interesting, specific-to-them educational conversations with someone who can talk to them about the future of their industry and business. Email and social are great, but these are methods to create more opportunities to sell on the phone or via video. Be different, do the hard things well, and results follow.
4. Millennials aren’t lazy: I hope nobody still buys into this fiction, but allow me to set your mind at ease. Today’s entry-level employees are driven, focused, ambitious, and hungry to learn. Nothing delights me more than a new ADR who walks in the door with a clear understanding of the value and skills they want to gain during their apprenticeship on my team. With this understanding, we can work together to give them those opportunities over the next 12-18 months, and build a transferable skill set for the next years of their career.
5. Micromanagement doesn’t work: I wrote much of this post on the way back from a week’s vacation, during which I was online for perhaps one hour, and my team was within five percent of a record week for meetings booked. The simple and evergreen lesson: Hire great people, train them well, give them clear outcome-oriented goals, and get out of the damn way.
6. Don’t overlook unconventional backgrounds when hiring: There’s a great line in the movie Boiler Room that goes “We don’t hire brokers here, we train new ones.” I worked briefly in commercial real estate before finding my way to SaaS sales. On my current team, we have folks who’ve been professional athletes, worked in optician’s shops, done customer service for trucking companies, and arrived straight from college. All are absolutely crushing the role, and I can see them them having long careers in sales. Great sales organizations can and should, accept experienced talent, but they should also strive to create a culture that’s perfectly comfortable hiring attitude and aptitude, and training for skills.
7. Empower people to be themselves: The most common mistake I see in newer managers is an attempt to duplicate their own style, quirks, processes, and workflow in their reps. There’s certainly a place for some of this (presumably you got promoted for a reason), but the job of a manager is to help people become the most actualized version of themselves via a consistent and disciplined iteration of process. The job of the manager is not to try and bottle something unique and magical and possibly unscalable.
8. Pay well: This one may be controversial, but so be it. Great talent is always cheap at the price, and pays for itself quickly. Here at Skilljar, we maintain a very, very high hiring bar and an “A players only” mindset. We make up for that by over-investing, both financially and in ongoing development programs. A huge thanks to the great Jason Lemkin for helping me figure this out.
9. Be mindful about burnout: Skilljar offers an unlimited-vacation policy and is respectful of work-life balance, and I encourage my team to take advantage of both. We live in a world of constant connectivity, endless distractions, and sales managers yelling about daily call metrics. Add in the constant rejection and prospecting grind inherent in an ADR role, and it’s little wonder that most sales organizations see this function as high-churn. I expect my reps to be fully engaged in everything they do at work and at home, and have minimal expectation of responsiveness after they leave the office. Many thanks as well to my boss (hi, Aashish!), who sets a great example by yelling at me to close my laptop and leave the office at least twice a week.
10. Don’t forget to celebrate: Skilljar is a high-growth organization with ambitions of helping all of our customers’ companies change the world through the adoption of their innovative products. It’s not easy, but it is rewarding, and we celebrate process improvements and victories in ways big and small (the Slack emoji game is very strong here). I’ve been fortunate to be a part of great teams and in great company outcomes in my time in tech. But, looking back on it, what I remember most are the people, the happy dances in the office when someone closed their first deal, the impromptu ice cream parties for a record week, the just-because praise, and thanks for assisting on a call. Now, as a manager, I try every day to recreate that same sense of adrenaline, fun, and groups pulling together towards a common goal. 
Does Skilljar sound like a place that you could call home? I’d love to hear from you! If you’re looking to break into SaaS Sales in Seattle, I’m hiring! Apply Here