Role Transition Discussion with Doug Green - May 20, 2025

Overview

Gary Sheng and Doug Green had a candid conversation about Doug's current job dissatisfaction and discussed a potential transition to a new sales leadership role at Alpha Schools. The conversation revealed Doug's frustration with lack of recognition, inequitable compensation structures within the organization, and his underutilized sales expertise. Gary proposed creating a dedicated sales team under Doug's leadership and outlined next steps for making this transition happen.

Key Topics

Doug's Current Job Dissatisfaction

Doug expressed significant frustration with his current role, primarily stemming from lack of recognition and unclear metrics for success:

Doug: "Just job completion satisfaction. I have none."

He shared an example of identifying and developing an intern whose project was ultimately purchased by Joe Liemandt, but Doug received no recognition:

Doug: "I identified John Allstammer immediately as a high-performing intern. I caught hold of him, developed him. Joe buys his project... No thanks."

Compensation Disparities

Doug highlighted two specific situations that triggered his dissatisfaction:

Doug: "I think what set me off was two things. One, I found out there was a commission of $450,000."

Gary: "Yeah, and with what results?"

Doug: "With what results. What qualifications."

Additionally, he described an uncomfortable situation with a potential commission:

Doug: "Shaz, who is like number 32 in Postmaster International worldwide, might need to accept a couple of people. And so Shaz gave me a set of cards. And he said, okay, but I'll need to pay you. And I didn't really know what the protocol was... It felt weird."

Proposed Sales Team Role

Gary identified that Doug's skills were being underutilized and proposed a transition to leading sales:

Gary: "Assuming that you could pass on this stuff to someone else, you should just be our – like you should be closing sales of students. You should be like literally getting back into sales and have commissions, right?"

Doug confirmed this aligns better with his skills:

Doug: "I mean, it's definitely where my sales team is focused most of the time."

Gary elaborated on the organizational gap:

Gary: "We don't have a sales team. This is one of my biggest gripes separate from, you know, your discomfort from your role. It's like someone needs to do it."

Current Untapped Opportunities

Doug revealed he already receives significant inbound interest:

Doug: "I have three to four people a week reach out to be able to do it."

Gary: "About Alpha?"

Doug: "Parents, potential partners."

Technology Integration for Sales

Gary outlined a vision for integrating AI into the sales process:

Gary: "I'm going to design this whole funnel, but if a parent gets excited about Alpha, they should be calling you. They should be calling you and your team. There should be some kind of AI routing process."

Doug recalled Gary's earlier idea about conversation tracking:

Doug: "I think that your listening thing is spot on... You were talking about wearing a device, a smart device that would transcribe conversations."

Gary: "Right, and then so literally every parent that calls us, we have psychographed... Because we can hear their voice. We can hear how they're reacting."

Action Plan & Next Steps

Gary proposed a specific path forward:

Gary: "I think the ideal role is where you get rewarded for performance, which is closing parents."

Gary: "I'm getting coffee with Mackenzie on Friday... I think I'm just going to get her buy-in to build out a sales team."

The plan includes:

1. Creating a detailed sales team structure
2. Doug leading this new department
3. Implementing commission-based compensation
4. Engineering support to build sales tech infrastructure
5. Potential tuition benefit for Doug's daughter Olivia

Gary: "I would just tough it out a little bit... Let's literally draft out a plan for a new sales team that you need... I advise on and then what I can do is basically get some engineers to build out whatever sales tech we need."

Emerging Technologies

Doug mentioned a new technology that could be relevant:

Doug: "I got this guy. I thought this was the coolest tech yesterday called Readology. And what it does is it aggregates all of your informal education. So when you're – it's in a browser extension... And then it creates credentials."

Key Insights

1. Underutilized Talent: Doug's sales expertise is not being leveraged in his current role managing interns.

2. Recognition Gap: Alpha appears to lack systems for acknowledging staff contributions to intern development.

3. Compensation Inconsistencies: Significant disparities exist in how different team members are compensated.

4. Missing Infrastructure: Despite significant parent and partner interest, Alpha lacks a dedicated sales team and process.

5. Technology Integration Opportunity: The discussion revealed potential for AI-enhanced sales processes that could leapfrog traditional approaches.

Next Steps

1. Gary and Doug to meet the following day to outline the ideal sales process
2. Gary scheduled to meet with Mackenzie to gain approval for creating a sales team
3. Doug to consider who could take over his current intern management responsibilities (potentially "Jack")
4. Explore implementation of HubSpot as a CRM solution
5. Develop compensation structure including base salary and commission