Jul 3, 2019 · 28m · saastr
Building a $100M ARR Sales Team the Second Time Around with WP Engine
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Matt Schatz, Senior Vice President of Sales at WP Engine, delivers a comprehensive masterclass on the strategic leadership, operational rigor, talent management, and cultural frameworks necessary to scale enterprise software sales teams beyond $100M in ARR.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.8 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 20:20 Dismissing founder's international management plan
Schatz recounts bluntly telling an expansion-stage CEO that two weekly one-on-ones with a foreign MD showed he fundamentally did not understand the required time commitment.
Hardest push from Jason ▶ 1:15 No host pushback in solo presentationThe episode is a solo conference keynote presentation without host moderation or pushback.
Biggest teaching moment ▶ 13:10 Differentiating lucky leads from sustainable sales excellenceSchatz explains to the audience why celebrating 150% quota attainment without inspecting conversion rates and inputs leads to false pedestals.
Jason holds their own ▶ 1:15 No host intervention presentThe host does not speak during this recorded conference talk.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Defining Employer Value Proposition and First Stories | 0 | 0 | 1 | 0 | In this solo conference presentation segment, Matt Schatz advises founders against using exits or easy ground-floor rhetoric as recruiting value propositions. Because the host is not participating in the monologue, host-side scores are zero. | |
| Recognizing and Setting C Players Free | 0 | 0 | 1 | 0 | Schatz explains why well-meaning C players must be transitioned out quickly to allow them to succeed elsewhere. The host is absent during this keynote monologue. | |
| Transitioning to Data-Driven Decisions and Input Science | 0 | 0 | 1 | 0 | Schatz emphasizes investing heavily in senior sales operations and evaluating granular input metrics rather than blindly celebrating top-line output numbers. | |
| Maintaining Fluidity in Sales Compensation Plans | 0 | 0 | 1 | 0 | Schatz discusses evolving comp plans and the significant time investment required to build trust in international offices, including a direct pushback he gave to an Austin founder. | |
| Fostering Culture and Sustaining Leadership Oxygen | 0 | 0 | 0 | 0 | Schatz defines culture as volunteering one's best and shares a closing lesson on leadership oxygen inspired by Sherpas in Nepal. |
Statements from this episode (13)
Schatz: Rackspace Grew From $1M to $870M Revenue Over Ten Years
“I spent my first 10 years at Rackspace. I was part of the team that helped grow that organization from about a million in revenue when I started to about eight hundred and seventy million when I left and threw an IPO.”
Schatz: WP Engine Has 90,000 Customers Across 140 Countries
“We now have about 90,000 customers in a 140 different countries.”
Schatz: WP Engine Hit $132M ARR After $250M Silver Lake Funding
“We're backed by Silverlake. Last year they made an investment of two hundred and fifty million into our business, and now we are doing about a hundred and thirty two million in revenue.”
Schatz: Only 0.4% of US startups ever reach $100M in revenue
“It's crazy to think I saw a stat that every year in the U.S., from all the companies that are founded, only .4% will ever hit a hundred million.”
Schatz: WP Engine Commits to Promoting Top SDRs in Nine Months
“But for my SDRs, my commitment to them is if they come in and overachieve, exceed expectations, I will promote them in nine months.”
Schatz: C players harm small organizations far more than large ones
“The problem that you run into is that a C player's impact on a small organization is far greater than a large organization. So you have to take action even quicker.”
Schatz: Hiring Junior Sales Ops Staff Costs Companies Far More Money
“Do not go junior here. It will cost you so much more money if you go junior here. When you go junior with your sales operations team or that sales operations person, you're gonna find somebody that can tell you all about the past. But at the speed and rate and…”
Schatz: Top sales performers will quit if managers do not challenge them
“If that's the conversation that you're having with an A player, that A player should fundamentally quit your organization. If you're not challenging them, they will quit, they should quit.”
Schatz: Sales compensation plans should constantly evolve with the business
“Your comp plans should be changing all the time. Your business is changing, so should your comp plans.”
Schatz: Early Rackspace Adjusted Sales Quotas Every Single Quarter
“At Rackspace in our early days, we were going through a really high growth time. We adjusted quotas every single quarter.”
Schatz: Opening International Offices Requires Relocating Top Headquarters Staff
“Part of that is invest in work permits. Invest in expat packages. Take one or two of your top people and send them over to that international office. If you don't do that, it's going to cost you so much more money in the long run because it's going to take so …”
Schatz: First International Country Managers Must Write Their Own Business Plans
“The other way to go and build trust across time zones is when you hire that first managing director or country manager, whoever that is, have them write the business plan. Don't write the business plan for themselves. Have them write it. Have them do the study…”