#124. Hold Department Heads To The Same Standard As Pro Coaches, General Catalysts Call Center VBO, vSaaS Summit Schedule
One vSaaS breakdown. One biz story. One 'how to'. In your inbox once a week.
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Alright, let’s get to it…
One ‘How-To’:
Hold You Department Heads To The Same Standards As A Professional Coach
Most SaaS company cultures are bean bags, happiness, “everything is all good” type of vibes.
For better or worse, we had the exact opposite.
I have a slightly unpopular (?) opinion — but I am somewhat unsure on why it’s unpopular if I’m being completely honest…
Exec performance = Wins & Losses
Just like professional coaches.
Every single department head owns one quantitative metric.
Sales owned ARR Bookings.
Customer Success owned Net Dollar Retention.
Product owned NPS.
Technology owned shipping X feature by X date with <X bugs
Finance owned ensuring we don’t go $1 over the expense plan.
You can debate the one metric but these worked for us.
But the important part is that they directly tie in with what the outside world is going to evaluate / value you’re business on.
PS - leaders that fought me on metrics the entire financial community agreed upon was a huge red flag. I ensured this was going to be ok in the interview process after dealing with previous leaders who would debate metrics every quarter versus just owning one.
We’d all spend a solid week or two on it at the start of every quarter. We’d negotiate it, we’d push back on one another, we’d ensure we were getting to a really intellectually honest place. No sandbagging.
After it was set, every executive knew that that metric was their job security. That I would judge them for their win loss record with that metric on a quarterly basis.
0-4? Out.
1-3? On thin ice.
2-2? Not good enough.
3-1? Good work.
4-0? Let’s talk a raise.
I’d have a public scoreboard on this.
The manager would then do the same thing for all their employees.
Their employees would be evaluated the exact same way. Except each employees number would add up to ~20% higher than their department goal.
Guess what? The board would then judge me on something ~20% lower than what I set with the executive team.
So now EVERY person in the company had a very clear quantitative milestone that added up to the overall companies performance.
Every person was responsible for tracking it EVERY week.
Our weekly executive meetings were set up around two particular items —
Where are we in terms of this one quantitative metric
What the problems were that were putting our one metric at risk, and how to solve said problems. Problem + Ideas for a solution. NEVER JUST A PROBLEM.
You can run an entire business with this process.
It’s a beautiful symphony if you do it right.
So a few questions to ask yourself:
Does the company have a quantitative north star?
Does each department leader have a quantitative quarterly goal that leads into the achievement of the company’s quantitative north star?
Does each employee have a quantitative quarterly goal that leads into the departments quantitative quarterly goal?
Does everyone get bonus’d on this and promoted/fired based on their wins and losses of said quarterly quantitative goal?
If you’re not doing all of these, think about adding it in.
I promise you it will change the trajectory of your business…
It sure did for us.
One vSaaS Breakdown:
Vertical Software Summit 2025
Checking in because the demand for this is kind of mind-blowing. We sold out of all sponsorships and have have confirmed ~100 high quality vSaaS founders, operators, investors, and acquirers. If you’re thinking about going, grab your ticket before they sell out!
I wanted to share our tentative conference schedule with you all — its going to be an epic two days.
October 17th Kick Off Party
8:00 PM – 11:30 PM
Start the summit with an evening of networking, drinks, and celebration at a beautiful Miami water-front mansion.
October 17th All Day Session
Breakfast & Networking
8:00 AM – 9:00 AM
Fuel up and connect with fellow vertical SaaS leaders to kick off the day.
Scaling Slice to a $1B+ VSaaS Co.
Speaker: Ilir Sela, Founder & CEO of Slice
9:00 AM – 10:00 AM
Learn how Slice scaled to a billion-dollar vertical SaaS company with actionable insights from its founder.
Scaling Your GTM from 7 Figures to 9 Figures
Speaker: Kyle Norton, CRO of Owner.com
10:00 AM – 10:45 AM
Discover proven go-to-market strategies to take your SaaS from 7 figures in ARR to 8 and 9 figures.
Is VSaaS Cool Again? A Discussion with VSaaS VCs
Speakers: Nic Poulos (Euclid VC), Nick Tippmann (TipTop VC), Coyne Lloyd (vSaaS Studio), Andrew Oved (Reformation Partners)
10:45 AM – 11:45 AM
Top vSaaS VC’s and Angels share their take on the resurgence of vertical SaaS, what they’re investing in, and what the future looks like.
Embedded Tooling for vSaaS Companies
Speakers: Hear from Raj Bhaskar (Founder & CEO of Tight) and a panel of vSaaS founders
11:45 AM – 12:15 PM
The history, the current state, and the future of embedded tooling for vSaaS companies and how to leverage them to drive revenue, improve retention, and increase TAM.
Lunch & Networking
12:15 PM – 1:15 PM
Enjoy a catered lunch while connecting with industry peers and speakers.
Venture Buyouts Panel
Speakers: Jeremy Yamaguchi (Cabana), Nathan Matthews (Roofer.com), Michael Stenclick (Tend & Atomic)
1:15 PM – 2:15 PM
Explore the world of venture buyouts with experts who are running tech + service business roll-up plays.
A Discussion with VSaaS Acquirers & Growth Equity Funds
Speakers: Sam Youssef (Valsoft), John Paterson (Quadshift), Dave Pandullo (Frontier Growth), and KC Wulff (Mainsail Partners)
2:15 PM – 3:15 PM
Gain insights from leading acquirers on what they look for when buying or doing majority investments in vertical SaaS businesses.
Coffee Break
3:15 PM – 3:30 PM
Recharge with coffee and casual conversations.
The First Major Vertical AI Exit with EvolutionIQ Co-Founder & Co-CEO’s
Speaker: Jonathan Lewin & Michael Saltzman of EvolutionIQ & Andrew Oved of Reformation Partners.
3:30 PM – 4:30 PM
Andrew Oved from Reformation Partners will interview the Co-Founders & Co-CEO’s of EvolutionIQ on what it takes to build & sell a massive Vertical AI business.
Building VSaaS for Laundromats into a Massive Business
Speaker: Alex Jekowsy, Founder & CEO of Cents
4:30 PM – 5:30 PM
Hear how Cents is transforming the laundromat industry and is aiming to build a billion-dollar vertical SaaS in a space everyone avoided.
Cocktails & Closing Happy Hour
Celebrate the vertical software community and wind down from an action-packed day with fellow founders, operators, and investors.
5:30 PM – 6:30 PM
So join Us in Miami this October!
Don’t miss this opportunity to be a part of the first ever Vertical Software Summit - where we will bring the community together for an epic few days. There is a limited number of slots for Founders/Investors/and vSaaS Vendors.
One Biz Story:
Crescendo:
General Catalysts Call Center Venture BuyOut
Hemant Taneja, CEO of General Catalyst did a write-up on of the call-center AI Venture Buy Out plays.
If you don’t know, GC raised a massive fund to attack this strategy. We’re talking billions they plan to pour into transform service companies.
Here’s the write-up:
At General Catalyst, we have a long and proud history of hatching companies – including Demandware, Datto, Kayak, and Livongo. These days we are particularly interested in scaled, legacy sectors where technology – and especially AI – can have an immediate, transformative effect, and where we can help accelerate this by bringing together the diverse talents required to build and scale these businesses.
The contact center business is one such area. It is massive - per Statista, the value of contact center billings is estimated to grow from $460 billion in 2022 to $741 billion in 2030. Further, 34% of the market and 15% of all white collar jobs in the US come from this industry, with Philippines and India having meaningful market share at 12% and 15% respectively.
Despite this scale and opportunity for impact, the industry has been slow to innovate. According to a Gartner report, contact center cloud adoption is at 12-15%, unlike peer categories like CRM with 55-60% cloud adoption. Most contact centers are seen as cost centers, and AI and cloud investments are often deprioritized. This impacts not only enterprises and contact center operators, but also has an adverse impact on the agents who have turnover rates of 30-35% per the same report due to workloads and burnout per SQM Group’s Research..
Artificial Intelligence and the advent of LLMs present both a threat and an opportunity to this sector. Given how many people are employed in this sector, getting this right is key. AI adoption is expected to reduce up to $80B in labor costs in contact centers by 2026, according to Gartner. But it also has the potential to turbo-charge customer service workers by making them more efficient, anticipatory and effective, ideally reducing burnout and turnover by automating the mundane work and improving job satisfaction. That said, in our view, for many contact centers AI is still an after-thought, especially the majority who haven’t migrated to the cloud.
We see a real opportunity to work with existing scaled players in this industry - namely world-class contact center operators who have the operational know-how to deliver the services day to day - and team them up with two new types of talents: the best AI-native engineers, who know how to build and fine-tune LLMs to make them work by leveraging the deep and rich insights from customer interactions and build increasingly automated resolutions loops, and leading CCaaS product minds who know where to focus on innovation vs re-inventing the wheel.
Today, we’re delighted to announce the result of that effort: Crescendo – one of the first vertically integrated, AI-native contact center businesses. We believe that vertically integrating the pieces and creating a feedback loop could result in industry leading automation of several scaled use cases. Using this IP, we believe we can drive material margin improvements in how contact centers are operated. This project brings together GC’s work in Creation and AI with our growing work in the US-India corridor.
To help build this business, we have partnered with Andy Lee, Matt Price and Dr. Slava Zhakov to be co-founders along with GC. Andy founded Alorica, the Gartner Magic Quadrant leader in contact centers with over $2B in revenue and built it without any outside funding. He is widely believed to be one of the best operators in this industry and combines deep industry knowledge and a track record of creating value with a beginners’ mindset of what AI can do to re-imagine the industry he has helped build. He is paired up with Matt who comes from building several 0-1 products and go-to market initiatives at Zendesk as SVP, joining there 3 years before their IPO and developing a successful decade-plus track record as a go-to leader with deep contact center industry expertise. Before joining us, Slava helped build Genesys from its early days and was a core contributor to their success as CTO. Between the founders, we have a team that has helped build four companies in this sector to over $1 billion in ARR. We believe the caliber of talent we’ve been able to attract is testament to GC’s ‘radical collaboration’ approach. This intentional pairing of talent, many of whom would not have encountered each other independently, is a critical aspect of our creation strategy.
In the initial stages, the goal is to build an AI-layer which creates playbooks that deliver automated resolution paths for repetitive contact center use cases as well as insights into how operations and customer satisfaction can be improved. We will prioritize 1-2 key verticals, and have already begun deploying our technology with early design partners. Our expectation: 10x+ productivity gains for agents and call center operators, while delivering a truly conversational experience for customers, all without long wait times. If done thoughtfully and in alignment with our Responsible AI manifesto, we believe this could be one of the most meaningful technology innovations directly introduced into contact centers in over two decades. We are joined in this by Alorica, who is participating as a strategic investor in Crescendo.
It is our privilege at GC to focus on an essential industry problem that touches so many of us - as agents, enterprise decision makers and most importantly as end consumers. We are honored to partner with Andy, Matt, Slava, as well as Alorica on this journey.
Have a product or service that would be great for our audience of vertical SaaS founders/operators/investors? Reply to this email or shoot us a note at ls@lukesophinos.com