Co-Founder & Chief Revenue Officer at Sales Assembly | Developing the GTM Teams of B2B Tech Companies | Investor | Sales Mentor | Decent Husband, Better Father

I’ve spent my career trying to solve one puzzle: how do you scale sales teams without losing what makes them great?

Before Sales Assembly, I lived the highs and lows of hyper-growth - leading revenue teams, juggling targets, and realizing that growth without structure eventually collapses under its own weight. The lesson stuck: great teams don’t just grow fast, they grow well.

That’s the idea behind Sales Assembly. We built the preeminent skill development platform for B2B tech companies: part training, part community, part therapy for GTM leaders trying to do more with less. We help teams move faster, stay aligned, and actually enjoy the process of getting better.

Somewhere along the way, I also became a General Partner at VentureOn Partners, Chapter Head at Pavilion, and mentor with Techstars. I’ve spent a lot of time with founders and operators who are chasing the same thing: building something that lasts without taking themselves too seriously.

A client and friend once described me as someone who “builds community through authenticity,” which I’ll take as the polite version of “tells it like it is.” That’s probably fair.

Outside of all that, I’m a decent husband, a better dad, and a walking Simpsons encyclopedia (seasons 1–11 only, of course). I travel when I can, laugh often, and still believe a good team - and a good joke - can get you through just about anything.

Matt Green

Your champion just rewrote your proposal in language her CFO would approve. She texted you on Saturday with intel from a leadership meeting you weren't in. Know what that looks like? 

Someone whose bonus depends on your deal closing.


Here's how one AE in the Sales Assembly ecosystem figured this out: 

She was working a MM deal that felt solid but wasn't moving. Champion was responsive, took every call, forwarded emails to the right people. Standard stuff. 

Then during a casual convo, she asked something she almost didn't: "You seem really motivated on this. What's going on?"

Turns out the champion's quarterly bonus was tied to getting this exact type of solution implemented before end of quarter. Her leadership had made it a goal. She needed this deal to close as badly as the AE did!


Believe it or not, everything changed after that. The champion started coaching the AE on exact language to use with her CEO. Shared what the CEO had said in a recent leadership meeting and suggested weaving it into the talk track. 

She'd gone from supporting the deal to co-building the pitch.


That deal closed. They still text each other to this day.


Now think about what DIDN'T happen. The AE didn't uncover this through a formal discovery framework. Instead, she asked one human question in a moment where she was paying attention.

And that's the thing very few folks teach in champion development. You can MEDDIC until you're blue in the face, but the single highest signal indicator of whether someone will actually fight for your deal is whether their compensation, promotion, or reputation depends on the outcome.


When someone's bonus is on the line: 

- They don't wait for you to ask for introductions. 
- They set up meetings before you request them. 
- They don't pass your proposal to procurement. They rewrite it. 
- They don't go quiet between calls. They reach out with intel you didn't know existed.

A friendly contact responds when you reach out. A real champion reaches out when you haven't. 


Do this exercise this week: On your three biggest open deals, can you answer these about your primary contact: 

1. What happens to their compensation or visibility if this project succeeds? 
2. What happens to them personally if it stalls? 
3. How are they measured on the initiative your solution supports?


If you can't answer those, really think hard about whether you actually have someone who will fight for your budget line in a room you're not in.

Sales Assembly facilitator Jon Rydberg nailed it: if there's no clear winner or loser when a deal dies, the deal is going to die. 

You can set your watch to it.

Co-Founder & Chief Revenue Officer at Sales Assembly | Helping B2B tech companies improve sales and post-sales performance | Decent Husband, Better Father

A CS leader in one of our peer groups tracks everything. NPS, CSAT, adoption, etc. Still got blindsided by three ENT churns last quarter. Combined $840K ARR = gone.

They had oodles of data at their fingertips, but they were measuring the wrong kind.

NPS tells you how customers felt last quarter.

Support tickets tell you what broke last week. 

Product adoption tells you what they did last month. 

All LAGGING indicators. By the time any of those metrics move, the decision to break up with you has already been made.


Leading indicators tell you what's GOING to happen. And there's real research backing up what stuff actually predicts churn before it shows up in a dashboard somewhere.

Login frequency is the most obvious one and the most ignored. HubSpot found that targeting users who dropped below one login per week cut churn by 15%. 

If someone stops showing up, the clock is ticking.


But logins alone miss the picture. Feature breadth matters more than raw engagement. 

Customers using 5+ core features churn at almost 1/3 the rate of single-feature users. The depth of adoption creates pain in the ass switching costs that no competitor can easily overcome. 

If your CSMs aren't tracking which features each account actually uses, they're flying blind on stickiness. And that's a shitty place to be when renewal season hits.


Another big one: WHO is logging in, not just how often. 

When admin and decision-maker engagement drops but regular users keep humming along, that's often the clearest signal your customer is shopping around. 

The people with budget authority are quietly shopping while their team keeps using your product out of habit. By the time the regular users notice, procurement already has three proposals on their desk.


The move here is to build a lightweight early warning system around 3 things. 

1. Login frequency trends by week, not month. 
2. Feature adoption breadth per account, tracked against your core value workflows. 
3. Stakeholder engagement patterns, specifically whether the economic buyer and admin users are still active or going dark.

None of this requires a new $100k CS platform. Pull login data from your product analytics. Cross-reference feature usage against your top five value-driving workflows. Flag any account where decision-maker activity dropped in the last 14 days. 

One Salesforce formula field or a simple dashboard in Gainsight or ChurnZero can automate most of it.

Lagging indicators tell you what's broken. Leading indicators tell you what's breaking.

While you can still fix it.

Associa

Business Development Manager

Vesta

Advisor

Destination UX 

Community-powered (STR) Airbnb property management platform

Connecting owners and guests with the local community

Our platform leverages an AI-powered community guide to connect guests to all of the information they need and all of the experiences they want. If our community guide is unable to help then our human hospitality team takes over while still leveraging our guest experience database.

We have designed a range of solutions to fit all types of owners and properties.
-STR Property Management 
-AI Destination Guide
-Acquisitions

Founder

Space Perspective

Talent Partner

Gamify

Director of Growth and Partnerships

IWG plc

Director of Partnerships & Growth

Market Gen

Founder and Head of Partnerships

Bluestone & Hockley Real Estate Services

-Grew social media engagement by 47%
-Closed business that created 7% Revenue growth in the company 
-Content creation

Director Of Business Development

Responsibilities:
-Social media marketing
-Event marketing 
-E-mail marketing
-Develop new business relationships with executive-level B2B clients, Investors, and board members
-CRM administration
-HOA/CAM management
-Residential management
-Commercial property management
-Identify new target markets

Comcast

Account Executive

Tandem Property Management, Inc.

Leasing and Marketing Manager

Hello, I'm Dallas, and I enjoy marketing startups, real estate, and travel. Since 2020, I've been actively involved in real estate investments and managing short-term rentals and in 2022, I founded a short term rental property management startup connecting owners and guests with the local community. 

Helping those around me get started in business ownership while building their community is something that I'm always interested in doing 

I like to talk about what I'm building here:
YouTube- Dallas Roark
Twitter @DallasRoark
Tik Tok @DallasRoark
Instagram @DallasRoark
LinkedIn @dallasroark

Interests include (but are not limited to):
-eSports
-Portland Trail Blazers
-Golf
-Tony Romo's Broadcasting
-Star Wars
-MTV Cribs style home tour videos 
-EDC 
-Travel
-Minimalism
-Athleisure clothing

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