8 Insights from 8 Weeks in High Growth SaaS Sales Leadership

DONE IS BETTER THAN PERFECT BECAUSE PERFECT NEVER GETS DONE        

? When you join early stage company (Seed or Series A; anything less than 100 employees), there is more to do than any one person can manage.

? Early in your tenure, you’re right to assume that doing quality work is important. That said, progress on key topics (instead of excellence) should be your personal measuring stick.

? There are likely 30+ reasons you landed this job; a top 3 reason you’re in the seat is that those hiring you believe you can make an impact quickly and with a relatively high degree of autonomy.

? There will be time to paint your masterpiece. In the early days focus on making demonstrable progress on a few key topics to help everyone at the company know they can count on you to produce results quickly.

TRYING TO ACCOMPLISH EVERYTHING AT ONCE SPREADS IMPACT TOO THIN        

What you think your boss is thinking for the first ~90 days:

? I'm so stoked for NEW HIRE to touch every single aspect of our business. Hubspot needs a refresher, training is happening piecemeal & our SDRs don't have a talk track for cold calls. We are paying this person well...time to see how many fires they can put out!

What your boss is actually thinking:

? I hope this new hire can stand up a semi-structured pipeline review call that’s worth a damn before our company offsite in 2 weeks.

? Your boss (even if that person is the CEO) also has a boss (the Board, their co-founders) to “sell”. The quicker you learn this the better off you’ll be. With their boss, they have time to highlight 1 or 2 things you've been working on. Make sure they don't need a full Notion workspace to keep track of those things.

TO DRIVE CHANGE EFFECTIVELY, THE "WHAT", "WHY" & "HOW" MUST BE SHARED EARLY AND OFTEN        

? While I’m not sure it every really worked (or if people just dealt with it more then), but the days of command and control leadership are finito.

? People have options of where they work. Unless you treat them with respect and consideration, they’ll exercise those options quicker than desired.

? This said, more important than people leaving your leadership (yes, often they leave leadership, not a company!), making sure people have their activity put on the right track is mission critical for driving impact. The trick here is making sure that “the right track” isn’t just some CTRL C / CTRL V from your last job.

? Make it clear you’ve assessed thing XYZ (the what) and because of reasons 123 (the why) we are going to move toward approach 456 so that we can improve ABC (the how).

? People are most inclined to change behavior when provided with context for how the change will benefit them, their careers & the business.

EXECUTE WITH FOCUS, COMMUNICATE REGULARLY & DEMONSTRATE THAT FEEDBACK HAS BEEN HEARD / IMPLEMENTED        

? In all likelihood, you were hired because leadership is already too busy / overwhelmed to manage everything that’s going on.

? Be a peach and make sure that you help to simplify their life rather than making it more complex.

Pro tips:

? Distill work streams into a simple one pager covering the week gone by and the 2 weeks to come.

? Recount feedback that was heard in the last 2 weeks and point to an example of where that feedback was implemented.

TO ACCELERATE PERSONAL GROWTH, JOIN A COMPANY THAT IS RAPIDLY GROWING ARR & THAT DEMONSTRATES A COMMITMENT TO GROWING ITS PEOPLE        

? My old CEO had many infamous quips. One of her most infamous ones was “growth can overshadow many shortcomings!”

? For any early stage company there are dozens (if not 100s) of things to build / processes to implement and enhance. If the sales aren’t growing - while keeping net revenue retention (NRR) in check -, the focus will regrettably shift toward incremental process honing rather than multiplying growth. It is far better to be on a loosely organized rocket ?? than a perfectly structured sinking ship ??.

? Assuming ARR growth is impressive and customers are sticking around after signature (a good sign the product / team offers recurring value), there should already be evidence of high output early stage employees now sitting in roles - yes, complete with new job titles! - that reflect greater responsibility.

? If leadership cannot point to examples of internal promotions within the organization, the promises of “we’re employee first” are likely empty.

RECRUITING IS THE PART-TIME JOB EVERY GROWTH COMPANY LEADER MUST BE READY TO EMBRACE        

? In the first year as a so-called Renaissance Rep in my first startup gig, I didn’t speak to a single recruit about growing the business.

? In my first 8 weeks at UserEvidence, I’ve met with 20+ people ranging from career changers vying for SDR roles, company switchers investigating AE slots and 15 year software industry vets that may well become my boss.

? I point this out not to throw shade ??♂? > I was an individual contributor for that entire year with the first company. At UserEvidence I’m responsible for our overall revenue targets.

? This said, you cannot reach orbital velocity without the right people in the rocket. If you’re not in always-on recruiting mode, you’re either not in leadership or you aren’t on a rocket ??.

SUCCESS IS THE COMPOUNDING EFFECT OF "LITTLE THINGS" BEING DONE IN A CONSISTENT, HIGH QUALITY WAY        

? The next big deal crosses the finish line and everyone gives Slack love to the AE for doing great work.

? The adulation is warranted because selling is hard (!!!) in any market is hard, but doing so in this tech climate can be brutal.

? Then, in the post-close analysis (which you gotta have as one of those core processes in the early stages), you take a good hard look at the full lifecycle of that 4 month, $50k win.

? Touch 1 > Engaging, thoughtful outreach from an SDR.

? Touch 2 > The AE walks through a deck Marketing helped piece together to ensure the common challenges are known and relatable.

? Touch 3 > CS joins the AE to review the onboarding process and ongoing support (a pain point from their previous vendor relationship).

? Touch 4 > AE is back in action with a demo, only this time they get to focus on a special feature Product just rolled out which nails the problem discussed in the original discussion.

? When everyone takes pride in their work and holds themselves to putting the customer first, no one has to be an omnipresent, omniscient all-star. Boring, I know.

BEFORE DEMANDING ACCOUNTABILITY FROM YOUR TEAMS, ORGANIZE TRAININGS THAT DEMONSTRATE & HELP DEFINE WHAT EXCELLENCE LOOKS LIKE        

? If you’re in sales, you’ve probably heard of the GIVE-GET matrix.

? If you’re not in sales, you’ve likely experienced this at play for most of your adult life.

? Want to get a lower interest rate on your mortgage, give a larger deposit.

? Want to get your kid in bed before 8:30, give them the promise of desert.

? Want to get your wife to pick up her shoes from the living room, give in to making the bed more regularly.

? If you want to hold people accountable (for quota, for activity levels, for nailing certain talk tracks, for all of the above ), you have to GIVE them the tools, resources, education, compassion and consistency they need to succeed.