Waycup Creative: Go-To-Market (GTM) Engineering & Multi-Channel Digital Marketing Strategy

Internal Document — Operational Vault
Author: Brenn Almario
Collaborator/Reviewer: Kevin Dockman
Date: July 1, 2026
Version: 1.0

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1. Executive Summary & Strategic Pivot

Waycup Creative is undergoing a foundational restructuring designed to maximize operational efficiency, transition to a performance-driven revenue model, and build a highly scalable client acquisition engine. Following the recent reduction of the Dog Wizard retainer (effective July 14, 2026), this strategy document establishes the concrete operational roadmap for the next phase of growth.

The Strategic Alignment

• Kevin Dockman: Focuses heavily on high-value client fulfillment, project management, and sales pipeline conversion.
• Brenn Almario: Transitions into Go-To-Market (GTM) Engineering, lead generation, tech-stack optimization, and proactive outreach.

This plan outlines a multi-channel framework with LinkedIn as the primary outbound engine, tightly integrated with HubSpot for Account-Based Marketing (ABM) and list segmentation, and structured around a rigid 2-week sprint model to maintain absolute execution focus.

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2. Financial Realignment & Performance-Based Commission Model

To mitigate the revenue contraction from traditional retainers, Waycup Creative is shifting toward a performance-based compensation framework for new client acquisition.

2.1 Framework for Commission Evaluation

Brenn Almario will evaluate and finalize a tiered structure that aligns compensation directly with high-margin, predictable revenue generation.

Metric / Milestone	Performance Incentive Type	Target Structure Options
Pay-Per-Meeting (SQL)	Fixed Cash Bonus	$150–$300 per qualified, completed discovery call.
Closed-Won (One-time Project)	Percentage of Contract Value	10% – 15% of total project revenue (payable upon client invoice settlement).
Closed-Won (Recurring Retainer)	Recurring Percentage	10% of monthly retainer for the first 6 months, or 7.5% for the life of the contract.
Performance Milestones	Scaled Bonus	Tiered bonus when total pipeline generated hits $50k,$100k, and $250k.

2.2 Financial Safeguards

• Minimum Lifetime Value (LTV) Floor: Incentives only trigger for clients onboarding at or above a minimum threshold (e.g., minimum $3,000projector$1,500/mo retainer).
• Clawback Clause: Commission payouts are structured alongside client payment cycles to insulate cash flow.

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3. Tool Optimization & Infrastructure: The HubSpot Audit

Before deploying outbound campaigns, the underlying infrastructure must be pristine. HubSpot will serve as the single source of truth for Waycup Creative’s ABM and CRM functions.

3.1 Immediate Audit & Cleanup Steps (Brenn Almario)

1. Data Hygiene & Deduplication: Run contact and company deduplication tools. Clean up orphaned records and legacy contacts from older campaigns.
2. Property Standardization: Ensure critical custom properties are mapped universally:
   • Lead Status: New, Attempted to Contact, In Progress, SQL, Closed-Lost.
   • Lifecycle Stage: Subscriber, Lead, MQL, SQL, Opportunity, Customer.
   • Target Account (Boolean): True/False (Crucial for HubSpot’s native ABM features).
3. Integration Health Check: Verify that LinkedIn Sales Navigator (if active), email tracking, and calendar scheduling integrations are fully operational.

3.2 List & Company Segmentation Matrix

To optimize targeting efficiency, data must be grouped into distinct tiers based on Waycup Creative’s Ideal Customer Profile (ICP):

[Total Addressable Market]
       │
       ├──► Tier 1: High-Value Enterprise/Mid-Market (ABM Target)
       │    └── Strategy: 1:1 Highly Personalized LinkedIn + Email Outreach
       │
       ├──► Tier 2: Standard ICP (Niche Focus - e.g., Professional Services)
       │    └── Strategy: Semi-Automated Sequences & Content Nurturing
       │
       └──► Tier 3: Low-Touch / Re-engagement (Past Leads & Inactive Accounts)
            └── Strategy: Bulk Value-Driven Email Inbound Campaigns

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4. Primary Channel Strategy: LinkedIn Outbound Engine

LinkedIn is designated as the primary channel for professional sales outreach and immediate pipeline injection. Outreach will be executed by Brenn Almario utilizing the account credentials provided by Kevin Dockman to maintain executive-level authority in the market.

4.1 Profile Optimization (The Landing Page Principle)

Before executing outbound messages, Kevin’s profile must be treated as a conversion landing page:

• Headline: Pivot from a passive title to a value statement: “Helping [Target Niche] Scale Through Digital Transformation & High-Performance Marketing Engine Operations.”
• About Section: Frame as a case study. Clearly highlight past successes (e.g., scaling retention, streamlining operational pipelines like CLG or Dog Wizard benchmarks).
• Featured Section: Pin a calendar booking link, a high-performing case study, or a text-based breakdown of Waycup Creative’s core service offering.

4.2 The Multi-Touch LinkedIn Outreach Playbook

Outreach must avoid looking like generic automation. The sequence below follows a high-touch, relationship-first protocol spread across 12 business days.

Day 1: The Soft Track

• Action: Profile view from Kevin’s account + Follow the target prospect.
• Objective: Trigger a notification on their device without forcing an interaction.

Day 3: Contextual Connection Request

• Action: Send a connection request. Crucial rule: No pitch.
• Template:

  “Hi [First Name], noticed your team at [Company] has been expanding your footprint in [Industry Vertical]. I’ve been analyzing how firms like yours navigate [Specific Industry Problem] this quarter. Would love to connect and keep up with your insights.”

Day 6: Value Drop (Post-Connection Acceptance)

• Action: Send a non-promotional asset, framework, or relevant case study.
• Template:

  “Thanks for connecting, [First Name]. I recently put together a short breakdown on how we reduced scope creep and doubled project output efficiency using a decentralized sprint model for one of our partners. Thought it might spark some ideas for your current operations: [Link to short text block or Notion/HubSpot page]. No reply needed, just thought you’d find it valuable!”

Day 10: The Soft Ask / Pattern Interrupt

• Action: Direct outreach targeting a specific operational bottleneck.
• Template:

  “Hey [First Name], quick question for you—how is [Company] currently tackling [Specific pain point, e.g., lead generation fragmentation / creative scaling]? We’re seeing a lot of teams struggling with [X] right now. If you’re open to it, I’d love to share two quick frameworks we use to solve this. Are you free for a brief 10-minute sync next Tuesday morning?“

4.3 Content Amplification (Inbound Support)

To support outbound efforts, Kevin’s profile should post 2-3 times per week. Brenn will assist in ghostwriting content focused on:

• Behind-the-scenes breakdowns: Dissecting the implementation of the 2-week sprint model.
• Strategic shifts: The death of bloated marketing retainers and the rise of performance-driven models (capitalizing on the real-world shift Waycup is making).

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5. Multi-Channel Marketing Plan: Secondary Channels

While LinkedIn drives immediate outbound conversations, a holistic multi-channel architecture ensures Waycup Creative captures demand across the entire market ecosystem.

┌─────────────────────────────────────────────────────────────────────────┐
│                     MULTI-CHANNEL ARRANGEMENT Matrix                    │
├───────────────────┬─────────────────────────────┬───────────────────────┤
│ Channel           │ Core Objective              │ Frequency / Cadence   │
├───────────────────┼─────────────────────────────┼───────────────────────┤
│ LinkedIn Outbound │ Direct SQL Generation       │ 20-30 prospects / day │
│ HubSpot Email     │ Content Nurturing & ABM     │ Bi-weekly sequences   │
│ Inbound Organic   │ Brand Equity & Authority    │ 2 posts / week        │
│ Referral/Partner  │ High-Trust Pipeline Spikes │ Monthly touchpoints   │
└───────────────────┴─────────────────────────────┴───────────────────────┘

5.1 HubSpot Email Sequences (ABM & Nurture)

• Cold/Warm Email Sequencing: For contacts segmented in HubSpot who do not engage on LinkedIn, build a parallel 3-step email track mimicking the value-first approach.
• Newsletter/Insights Broadcast: Transition the existing database through a bi-weekly automated email that delivers tactical advice (e.g., “How to prevent scope creep in creative projects”). Keep Waycup Creative top-of-mind.

5.2 Referral Network & Strategic Partnerships

• Leverage existing client relationships (e.g., dog training networks via Dog Wizard legacy networks, corporate networks via CLG).
• Create an explicit referral incentive framework: Provide a 10% introductory credit or cash payout for verified agency introductions.

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6. Sales Operations & Immediate Pipeline Management

Waycup Creative currently has 4 active prospects sitting in the pipeline. These represent the immediate path to revenue stabilization and must be managed with extreme precision alongside new outbound generation.

6.1 Action Plan for Active Prospects

1. Pipeline Mapping: Move all 4 active prospects into a dedicated HubSpot Deal Stage (e.g., Discovery Call Completed or Proposal Pending).
2. Deal Audit: For each prospect, document:
   • What is the explicit operational pain point?
   • What is the specific blocker to closing (Budget, Timing, Authority)?
   • When was the last contact date?
3. Bespoke Re-engagement Sequence: Do not send generic follow-ups (“Just checking in”). Instead, send a tailored asset or localized audit specific to their business challenge within the next 48 hours.

6.2 Weekly Sales Cadence

• Pipeline Review Meeting: A strict, 30-minute Monday morning alignment between Kevin and Brenn.
• Metrics Reviewed: Total New Conversations Started, Discovery Calls Booked, Pipeline Velocity (deals moving forward), Blocked Deals.

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7. Execution Framework: The 2-Week Sprint Model

To maximize output and eliminate the scope creep that historically degrades agency margins (as noted in the CLG client account review), Waycup Creative will run both its client delivery and its internal marketing strategy using a 2-week sprint model.

7.1 Operational Sprint Rules

• Hyper-Focus Limitation: Project/Internal output is restricted to 1 or 2 defined goals per sprint. Anything else is pushed to the backlog.
• Sprint Planning: Every alternate Friday, Brenn and Kevin define the deliverables for the upcoming sprint.
• Sprint Retrospective: Evaluate what caused friction, adjustments needed for the performance compensation tracking, and tool efficiency gaps.

7.2 Core Deliverables Matrix (Sprint 1 & Sprint 2 Concept)

Sprint 1: Infrastructure & Foundation Launch

• Goal 1: Complete full HubSpot CRM Audit, contact deduplication, and target account list segmentation.
• Goal 2: Optimize Kevin’s LinkedIn profile for conversion and clear outbound outreach configurations.

Sprint 2: Outbound Engine Deployment & Deal Execution

• Goal 1: Launch the LinkedIn multi-touch sequence targeting Tier 1 accounts (Minimum 100 highly personalized touchpoints).
• Goal 2: Execute bespoke re-engagement strategies for the 4 active pipeline prospects to push for closed-won status.

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8. Key Performance Indicators (KPIs) & Dashboard Setup

Progress will be measured quantitatively to ensure the GTM engineering efforts directly fuel the performance-based revenue targets.

• Activity Metrics (Brenn):
  • Accounts Audited and Segmented per Sprint: Target 150+
  • Daily LinkedIn Touchpoints (Connections + Follow-ups): Target 25-30/day
• Conversion Metrics (Joint):
  • LinkedIn Connection Acceptance Rate: Target >30%
  • Positive Response / Conversation Rate: Target 10% of accepted connections
  • Discovery Calls Booked (SQLs): Target 4 per month
• Financial Metrics (Waycup):
  • Pipeline Value Generated: Target $20,000+ rolling value
  • New Performance-Based Revenue Contract Value: Target $5,000/mo run-rate replacement by end of Q3.