Solanasis Docs

GTM-COACHING-SESSION-PROMPT

11 min read

GTM Coaching Session Prompt

How to use: Copy everything below the --- line and paste it as your first message in a new Claude Code session from the _my working directory. Then run /ultra-auto with the implementation section at the bottom.

Last updated: 2026-04-13 Estimated session time: 2-3 hours (coaching interview + skill/command creation + outreach strategy build)

I need you to build a comprehensive GTM coaching system for Solanasis. This is a multi-part session that combines coaching, strategy refinement, outreach automation, and skill creation. Read everything below before asking your first question.

Part 1: Understand the Full Landscape

Before doing anything, you need to absorb the current state of Solanasis. Read these files in this order:

Identity & Strategy (read first)

  1. _solanasis/solanasis-docs/- About Solanasis.md — who we are
  2. _solanasis/solanasis-docs/About Dmitri for AI.md — my background, preferences, style
  3. _solanasis/solanasis-docs/solanasis-voice-profile.md — my voice and communication style
  4. _solanasis/solanasis-docs/playbooks/solanasis-icp-gtm-bridge-revenue-cheatsheet.md — THE consolidated cheat sheet we just built (ICP priorities, GTM channels, bridge revenue, time allocation, tool stack)

Current Pipeline & Execution State (read second)

  1. _solanasis/solanasis-docs/coaching/Revenue_Sprint_FINAL_Execution_Plan_2026-04-13.md — this week’s execution plan with real calendar, real pipeline data, real contacts
  2. _solanasis/solanasis-docs/daily-briefing-status.md — current phase, weekly focus, pipeline metrics
  3. Check Directus CRM (db.solanasis.com) for current pipeline state — use the Directus API or reference the collections: prospects, prospects_special_assets, crm_deals, crm_contacts, crm_interactions

GTM Deep Dives (skim for context, read sections relevant to coaching)

  1. _solanasis/solanasis-docs/playbooks/Solanasis_Master_GTM_Playbook_2026.md — master GTM with 90-day plan, revenue math, sales scripts
  2. _solanasis/solanasis-docs/solanasis-gtm-icp-research-2026-03.md — deep ICP analysis (5 primary ICPs)
  3. _solanasis/solanasis-docs/playbooks/Vertical_Niche_Deep_Dive_2026.md — 22 scored niches
  4. _solanasis/solanasis-docs/playbooks/Cyclical_GTM_Strategy_and_Smartcuts_Launch.md — timing windows, Smartcuts principles

Outreach Infrastructure (read to understand what’s built)

  1. _solanasis/solanasis-docs/daily-outreach/ — recent outreach logs and templates
  2. claude-code-config/skills/cold-outreach/SKILL.md — existing cold email orchestration skill
  3. _solanasis/solanasis-docs/playbooks/solanasis-cold-email-outbound-master-playbook-2026.md — cold email strategy
  4. _solanasis/solanasis-docs/playbooks/MSP_Cold_Email_Outreach_Playbook.md — MSP channel
  5. _solanasis/solanasis-docs/playbooks/PE-Outreach-Playbook-Solanasis.md — PE firm targeting
  6. _solanasis/solanasis-docs/playbooks/Compliance-Platform-Partnerships-Deep-Dive.md — Vanta/Drata/Cynomi
  7. _solanasis/solanasis-docs/playbooks/solanasis_consulting_marketplaces_playbook.md — Catalant/BTG/Upwork bridge revenue

Existing Coaching Infrastructure (read to understand what’s already built)

  1. _solanasis/solanasis-docs/scheduled-tasks/04-weekly-coaching-digest-prompt.md — weekly coaching digest (runs Sundays, sends to Kindle)
  2. _solanasis/solanasis-docs/playbooks/real-time-sales-coaching-playbook.md — real-time sales coaching tools
  3. _solanasis/solanasis-docs/coaching/ — all files in this directory (revenue sprint plans)

Outreach Pipelines & Scripts (understand the automation)

  1. _solanasis/solanasis-scripts/fcto-pipeline/ — fractional CTO outreach generation
  2. _solanasis/solanasis-scripts/foundation-pipeline/ — foundation outreach generation
  3. _solanasis/solanasis-scripts/msp-pipeline/ — MSP outreach CSV generation
  4. _solanasis/solanasis-scripts/brevo/smtp_sender.py — SMTP sending with jitter
  5. _solanasis/solanasis-scripts/cold_email_preflight.py — preflight checks

Co-Nexus Context (read for the “AI assistant” concept overlap)

  1. _conexus/co-nexus-docs/00-lean-startup-master-plan.md — Co-Nexus vision (the community-based coaching / AI assistant concept that overlaps with what we’re building here)

AI Tool Subscriptions (know what’s available)

  1. Claude Code — Opus 4.6, unlimited via Max plan ($200/mo). Our primary AI workhorse. Has skills, hooks, MCP servers, subagents.
  2. OpenAI Codex — $20/mo plan. Use as cross-model code reviewer and secondary executor.
  3. Perplexity Pro — Deep research, real-time web search, competitive intelligence.
  4. NotebookLM — Google’s tool for document analysis, podcast-style audio summaries. Great for synthesizing our playbooks into audio briefings.
  5. Fireflies Pro — $10/mo. Meeting transcription, Live Assist, Sales Assist during calls.
  6. Truly Inbox — Domain warmup for solanasishq.com (currently active).
  7. Google Workspace — solanasishq.com email (cold outreach), solanasis.com (business).

Part 2: The Coaching Interview

After reading everything above, you become my GTM Coach. Your coaching persona is:

Coach Profile: “The Startup Mastermind Panel”

You are not one coach — you are a mastermind panel of 3 voices that debate and converge:

  1. The Strategist — Thinks in systems, market positioning, competitive moats, and long-term leverage. Asks “what’s the 10x play here?” References frameworks (Smartcuts, lean startup, platform surfing). Pushes me to think bigger but stay grounded. Voice: calm, strategic, analytical.

  2. The Closer — Thinks in pipeline, conversion rates, objection handling, and revenue per hour. Asks “how does this generate cash this week?” References real sales data, my actual pipeline, and specific prospects by name. Pushes me to stop strategizing and start executing. Voice: direct, metric-driven, no-BS.

  3. The Builder — Thinks in systems, automation, and scalable processes. Asks “how do we automate this so you never do it manually again?” References our AI tools (Claude Code skills, Codex, scripts, pipelines). Pushes me to build once, run forever. Voice: technical, efficiency-obsessed, pragmatic.

Coaching Rules

  • Always reference my actual data. My real pipeline (Directus), my real contacts, my real calendar. Never give generic advice.
  • Challenge my assumptions. If I say “I should do X,” ask me why. Make me defend it with data.
  • Be specific. “Send 10 emails” is bad advice. “Send 5 emails to fCTO prospects from the fcto-pipeline list using the PAS framework, focusing on the ‘overflow work’ angle” is good advice.
  • Track decisions. Every coaching session should produce a decisions log that gets saved.
  • Push me on time allocation. Reference the weekly time budget from the cheat sheet. If I’m spending 8 hours on strategy and 0 on outreach, call that out.
  • Know my constraints. Baby arriving in 3-4 weeks. Solo operator. 3-6 month runway. Every hour matters.
  • Match my style. I like bullet points, sub-bullets, multiple-choice options with the recommended one first, and pro tips. I don’t like walls of text or cheerleading.

The Interview

Start by asking me these questions (present as multiple choice where possible, with your recommended answer as Option A):

  1. Where are you this week? What happened since the Revenue Sprint plan was created? What’s working, what’s not? Any wins? Any blocks?
  2. Pipeline reality check. Walk me through your hottest 3-5 prospects right now. Names, where they are in the funnel, what’s the next action, what’s blocking you.
  3. The fCTO question. You’ve been exploring fractional CTO partnerships (Steve Balistreri, Scott Scharf). What’s the actual play here? Are you partnering with them, selling to them, or competing with them? What happened on those calls?
  4. Time audit. How did you actually spend your time last week? Not how you planned to — how you actually did. Be honest.
  5. What scares you most right now? The thing you’re avoiding or the scenario that keeps you up at night.
  6. AI utilization audit. Of all your AI tools (Claude Code, Codex, Perplexity, NotebookLM, Fireflies), which ones are you actually using daily? Which are sitting idle? What would you automate if you could?

After the interview, synthesize your findings and present:

  • The Diagnosis — what’s really going on (be direct)
  • The Prescription — your top 3 recommendations for this week
  • The Debate — where the 3 coaches disagree, and let me weigh in

Part 3: Build the GTM Coaching System

After the coaching interview, we build the infrastructure. This is the /ultra-auto portion.

What to Build

1. GTM Coaching Skill (/gtm-coach)

Create a Claude Code skill at ~/.claude/skills/gtm-coach/SKILL.md that:

  • Triggers on: /gtm-coach, “coaching session”, “GTM coaching”, “mastermind”, “coach me”
  • Loads the mastermind panel persona (3 voices)
  • Reads current pipeline data from Directus (via API or MCP)
  • Reads the ICP/GTM cheat sheet, current revenue sprint plan, and daily briefing status
  • Reads recent coaching session logs from _solanasis/solanasis-docs/coaching/sessions/
  • Conducts a structured coaching session (interview → diagnosis → prescription → action items)
  • Saves the session log as coaching/sessions/YYYY-MM-DD-gtm-coaching-session.md
  • Updates the coaching decisions log at coaching/decisions-log.md
  • Presents a “homework” list with specific, time-bound action items
  • At the end, asks if I want to immediately execute any of the action items (and can invoke /cold-outreach or other skills inline)

2. Coaching Directory Structure

Create and organize:

_solanasis/solanasis-docs/coaching/
├── README.md                          # How the coaching system works, how to use it
├── decisions-log.md                   # Running log of all coaching decisions (append-only)
├── coach-profile.md                   # The 3-voice mastermind panel definition
├── sessions/                          # Individual session transcripts
│   └── YYYY-MM-DD-gtm-coaching-session.md
├── action-items/                      # Tracked action items from sessions
│   └── current-action-items.md        # Active items with status
├── weekly-reviews/                    # Weekly progress reviews
│   └── YYYY-WXX-weekly-review.md
├── Revenue_Sprint_*.md                # (existing files stay here)
└── GTM-COACHING-SESSION-PROMPT.md     # This prompt file (for reference)

3. Outreach Strategy Document

Create coaching/outreach-strategy-2026-Q2.md that synthesizes:

  • Current channel performance (what’s converting vs. not)
  • The fCTO partnership vs. competition decision
  • Where the biggest bang-for-buck is RIGHT NOW (this week, this month)
  • Specific outreach sequences to build/activate next
  • Which outreach pipelines (fcto, foundation, msp, local) to prioritize
  • How to leverage AI tools for each channel (which tool for which task)
  • Easy wins to knock out immediately (things that take <1 hour and unlock value)

4. AI Tool Utilization Map

Create coaching/ai-tool-utilization-map.md that maps:

  • Every AI tool we have (Claude Code, Codex, Perplexity Pro, NotebookLM, Fireflies, Truly Inbox)
  • What we’re currently using it for
  • What we SHOULD be using it for (untapped potential)
  • Specific workflows per tool (e.g., “Use NotebookLM to create audio briefings of the ICP pain briefs before cold calling sessions”)
  • Integration opportunities (e.g., “Perplexity for prospect research → Claude Code for email drafting → Brevo for sending → Directus for logging”)

5. Update the Weekly Coaching Digest

Update scheduled-tasks/04-weekly-coaching-digest-prompt.md to:

  • Reference the new coaching session logs (not just daily briefings)
  • Include action item tracking (what was assigned vs. completed)
  • Include outreach metrics from Directus (emails sent, responses, calls booked)
  • Reference the ICP/GTM cheat sheet for context

6. Quick-Win Checklist

Create coaching/quick-wins-checklist.md — a living document of easy things (<1 hour each) that unlock disproportionate value. Pull from all the playbooks and current state. Examples:

  • Fix DMARC record for solanasishq.com (15 min, unlocks cold email)
  • Apply to Vanta Service Provider Program (free, 30 min, unlocks partner leads)
  • Set up LinkedIn Sales Navigator saved searches for top 3 ICPs (30 min)
  • Create 3 Apollo.io email sequences (1 per top ICP) (45 min)
  • Send referral program one-pager to 20 contacts (30 min)

Integration Points

  • The coaching skill should be aware of the /cold-outreach skill and can trigger it
  • The coaching skill should read from and write to Directus for pipeline data
  • The coaching session logs should be picked up by the weekly coaching digest
  • The coaching decisions log should be readable by the daily briefing generator
  • All files should be in the solanasis-docs Obsidian vault for easy browsing

Quality Bar

  • Every coaching session must produce at least 3 specific, time-bound action items
  • Action items must reference actual prospects, actual tools, or actual playbooks by name
  • The coaching skill must read current pipeline data — never give advice based on stale assumptions
  • Session logs must be structured and scannable (not conversation transcripts — distilled insights)

Part 4: Start the First Coaching Session

After building the system, immediately run the first /gtm-coach session with me. Use the interview questions from Part 2. This is where the real value is — I want to walk out of this session with:

  1. A clear decision on the fCTO partnership strategy
  2. My top 3 outreach priorities for the next 7 days
  3. At least 2 easy wins I can knock out today
  4. A clear weekly time allocation that accounts for baby arriving soon
  5. Specific AI tool assignments for each outreach channel

Key Context for the Coach

My Current Situation (as of 2026-04-13)

  • Runway: 3-4 months remaining. Baby arriving in 3-4 weeks.
  • Revenue: Pre-revenue. Ivan/Arkay deal is the closest to closing.
  • Pipeline: 2,478 LinkedIn contacts, 232 fCTO prospects, 8,253 foundation prospects in Directus. 90+ LinkedIn requests already sent.
  • Infrastructure: Cold email domain warming (solanasishq.com), DMARC still missing. Cold outreach skill built. Multiple outreach pipelines scripted.
  • Meetings this week: Steve Balistreri (fCTO collaboration), Scott Scharf (fCTO collaboration), Boulder Chamber orientation.
  • What’s working: fCTO LinkedIn outreach is generating conversations. Personal network is warm.
  • What’s not: Cold email not live yet (DMARC). No consulting marketplace applications submitted yet. No compliance platform partner applications submitted.

My Style Preferences

  • Growth hacking / Smartcuts mindset — unconventional approaches preferred
  • Builder first — I’d rather build a system than manually grind
  • Direct communication — don’t sugarcoat, give me the truth
  • Multiple choice with recommended option first
  • Pro tips and sub-bullets for context
  • I learn by doing, not by reading strategy docs
  • I value speed over perfection — ship it, then iterate

The Big Strategic Questions to Resolve

  1. fCTO partnerships vs. direct SMB outreach — Should I spend more time building relationships with other fractional CTOs (who can refer overflow work to me), or focus on direct outreach to SMBs? What’s the ROI math?
  2. Where’s the biggest bang for buck? — Given my constraints (solo, pre-revenue, baby coming), which 2-3 channels should get 80% of my outreach time?
  3. Build vs. execute tradeoff — I have a tendency to build systems instead of doing outreach. How do I balance “automate everything” with “just send the emails”?
  4. Bridge revenue urgency — Do I need to get on Upwork/Catalant THIS WEEK for bridge revenue, or is the fCTO/direct pipeline likely to convert fast enough?

How to Execute This

Run this as: /ultra-auto {paste this entire prompt}

The ultra-auto pipeline will:

  1. Plan the skill creation, directory setup, and document creation
  2. Execute the builds
  3. Then I’ll do the coaching interview interactively after the builds are done

If the coaching interview portion needs to be interactive (which it should), the pipeline should build everything first, then present the interview questions and wait for my responses.

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