One of my biggest mistakes while running PlanGrid was not paying enough attention to sales operations, particularly around quota planning and territory assignments. Our quota over assignment revolved around 40%, from the front-line reps all the way up to the head of sales. In other words, we assigned 40% more street quota than our actual company revenue target.
Even though we hit our aggressive triple-digit growth goals during those years, we weren’t able to generate the pipeline needed for every rep to succeed. As a result, many sales reps consistently missed their targets, leading to high turnover.
My board taught me to focus obsessively on financial metrics like magic number, NDR, gross margin, churn, which are all important. But these metrics offer an incomplete view of the business, as they’re far removed from the day-to-day reality and culture of the customer facing organization.
Hindsight is 20/20.
In 2016–2018, most of our sales team wasn't hitting quota, even though the head of sales and company did. That’s a broken model. A small percentage of top performers carried the team, while the majority of the team struggled to hit their OTE.
Many reps weren’t making enough to support their families. Naturally, they self-selected out. That attrition came at a high cost: we lost tribal knowledge, had to spend time and resources recruiting replacements, and then had to ramp new hires from scratch.
If I could timewarp back to 2015, when our first sales reps joined, here’s what I would do differently:
1. Limit Quota Overassignment (low single digits)
This would place more responsibility on managers to help their teams succeed and align the full organization around achievable goals.
2. Ensure Equitable Territories
With a land-and-expand business, new reps without a renewal base had no realistic shot at hitting their OTE in year one. If we had allowed managers to participate in territory planning and fairly distribute accounts, we could have better retained talent and improved team wide performance. Transparency is key. It would have relieved a lot of disputes about account assignments.
3. Adjust Quotas in Down Years
No one enjoys hitting only 70% of quota, regardless of the number. People don’t wake up aiming to do a C-minus job. In years when the majority of the team was significantly below target, we should have reduced quotas to protect morale and performance.
Our HR team estimated that it cost about $7,000 to hire a sales or marketing employee, and $10,000 per engineering hire (just for sourcing, process, and interviews)*. Attrition is expensive.
*Note: these benchmarks are from the mid 2010s.
4. Ask Better Questions
A few critical questions to revisit regularly:
"How do we raise the bar without breaking the team?"
"Who carries the weight, reps, managers, or leaders?" and “Does our compensation reflect that?”
"Which segments do we double down on, and where do we shift territories to maximize growth.”
Tracy Young, the co-founder and CEO of TigerEye and former leader of PlanGrid, has a proven track record in scaling tech enterprises, notably leading PlanGrid to a $875 million acquisition by Autodesk in 2018. She is recognized in Forbes’ Top 50 Women in Tech, has spoken at prestigious events like TEDWomen 2020, and holds a B.S. in construction engineering management.
