🎙️ Session: 30 09:20 CDT - Notes by Gemini

Daily Huddle - June 30, 2026

Executive Summary

A critical daily huddle on June 30, 2026, between Kevin Dockman and Brenn Almario addressed an immediate financial challenge: Dog Wizard cutting its retainer in half starting July 14th. This substantial revenue reduction necessitates a strategic pivot from the current hourly retainer model to a performance-based or commission-only compensation structure for Brenn, effective after a two-week transition period for which an advance payment has been made.

The new operational focus places Kevin on existing client work and managing the sales pipeline, while Brenn transitions fully into a Go-to-Market (GTM) engineering role, concentrating on lead generation, market strategy development, HubSpot optimization, and LinkedIn outreach. Administrative restructuring also includes internalizing bookkeeping. For client management, a two-week sprint model will be implemented for the CLG client to better manage scope and task volume. The immediate priority is for Brenn to define financial goals under the new model, draft a GTM strategy, and initiate sales activities to secure new clients and ensure business growth.

Key Architectural Frameworks & Core Principles

• Performance-Based Compensation Model: A fundamental shift from hourly retainers to a commission-only or performance-based structure, directly tying Brenn’s compensation to success in client acquisition and sales growth for Wake Up.
• Go-to-Market (GTM) Engineering & Sales Specialization: Clear role delineation with Kevin focusing on Fractional CTO client work and existing sales pipeline, and Brenn dedicated to GTM strategy, lead generation, account-based marketing (ABM) utilizing HubSpot, and professional sales outreach via LinkedIn.
• Account-Based Marketing (ABM) & HubSpot Maximization: Leveraging HubSpot’s advanced features for targeted account research, market segmentation, and streamlined sales processes to efficiently identify and engage potential fractional CTO clients.
• Structured Client Project Management (2-Week Sprints): Implementing a two-week sprint model for client engagements (e.g., CLG) to define focused deliverables, manage scope creep, and ensure efficient task completion, with the principle of “if you want to add something, you have to remove something.”
• Administrative Efficiency & Internalization: Reducing overhead by terminating the external bookkeeper and moving financial management tasks in-house, potentially integrating them with business development learning opportunities.

Flight Plan Action Items

• [Brenn Almario] Evaluate commission model: Evaluate the performance-based commission model and determine financial goals for the next contract phase.
• [Brenn Almario] Create marketing strategy: Draft a plan for go-to-market engineering and sales efforts in a markdown file and upload it to the vault.
• [Brenn Almario] Conduct LinkedIn outreach: Execute professional sales outreach using the account credentials provided by Kevin.
• [Brenn Almario] Audit HubSpot: Review current data and tool configurations to prepare for upcoming sales and marketing activities.
• [Brenn Almario] Segment contacts: Organize and segment existing contact and company lists to improve targeting efficiency.

Key Structural Sections of the Discussion

• Dog Wizard Retainer Reduction & Immediate Financial Action:

  • Kevin Dockman (00:20:54): “So, Dog Wizard wants to cut their retainer in half. So, budget problems have gotten worse. And here’s what I want to do. So, I paid I I sent the wires for your last invoice, latest invoice, and I already sent you two weeks for the next two weeks, just as like a we’re definitely going to do that… my second check from them is going to be half. We’re immediately going to drop to half at the 14th.”

• Proposed Shift to Performance-Based Compensation Model:

  • Kevin Dockman (00:21:38): “If we get clients quickly, then we just keep going… I think we just need to move to a commissiononly model or like a performance-based model where if you can book meetings, if you can get, you know, a meeting booked, we’ll come up with some dollar amount that tries to make it as close to 1,600 a month as possible for that success. But we h I have to get new clients basically.”
  • Kevin Dockman (00:25:56): “The current structure of the contract, the way we started it in February is going to end. I’m giving you basically that two weeks notice now on July 14th for the current contract. We will write up a new one, right, for what that’s going to look like.”

• Brenn’s Response & Commitment:

  • Brenn Almario (00:24:20): “For me I uh uh on my standpoint I I don’t really have any choice. So as much as possible if there’s you know what is on our plate then I’m going to eat it.”
  • Brenn Almario (00:25:03): “I’ve been gaining more knowledge and at the same time I’ve been working with you and yeah, I don’t really want to like on my opinion like I don’t want to find another job because I’ve been enjoying working with you Kevin honestly.”

• Bookkeeping & Administrative Restructuring:

  • Kevin Dockman (00:26:58): “The other thing I did, and I was going to do this anyway, is I fired my bookkeeper yesterday or gave them notice this morning. I was only paying them 200 bucks a month. It’s either going to be my wife who I’m who payroll starts for tomorrow, or like, you know, you can help me with that.”

• New Role Specialization & Focus:

  • Kevin Dockman (00:29:53): “I’m going to focus on client HubSpot, client work, client whatever, and I need you to focus on wake up work, wake up HubSpot, wake up, you know, things like that.”
  • Kevin Dockman (00:30:26): “I think that’s it’s that’s your bread and butter. It’s where you shine and um you can still learn continue to learn obviously AI and a lot of this integration stuff on the wakeup side and if and when there’s ever like a hey man I just really need your help on this client or whatever you know I’ll we’ll do up like a bucket of hours.”

• Client Management for CLG (Two-Week Sprint Model):

  • Kevin Dockman (00:37:25): “I got to have a tough conversation with CLG. They’re just they’re they’re they’re they’re upset, but they’re only upset because and this is what where Noel always failed is they they they’re severely misunderstanding the scope of work.”
  • Kevin Dockman (00:38:15): “Pick the task for the week or two tasks for the week. We’ll work on it for the week. We’ll do a two-eek sprint and we can move to a twoe sprint model and say this is going to be done in two weeks or it’s not. Otherwise, I can’t work on all eight things at once… if you want to add something, you have to remove something.”

• Go-to-Market Strategy Development & Tooling:

  • Kevin Dockman (00:34:54): “The strategy for growth involves leveraging the full capabilities of HubSpot, specifically focusing on account-based marketing, market research, and segmenting existing contact lists. Brenn is tasked with using the next two weeks to study HubSpot features and prepare a blueprint for client acquisition.”
  • Kevin Dockman (00:39:57): “Do a planning session and build an artifact and build a blueprint for like what’s the what are the steps to knock this out based on everything that’s in the vault like everything that’s missing, all the assets we have, the assets we don’t have, and what needs to get done.”
  • Kevin Dockman (00:40:24): “I really think LinkedIn is probably the biggest focus.”
  • Kevin Dockman (00:41:41): “I just moved my LinkedIn to the wakeup vault in one pass instead of my employee vault.”
  • Brenn Almario (00:41:41): “I’ll check your HubSpot and check also those contracts being segmented… create a a plan for your what we call as marketing strategy.”