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Breakthrough Career Coaching By Stephen Drumm · Tech Sales, GTM & AI
⚡ Packages Apply for 1:1 Coaching →
BreakthroughCareerCoaching.com · 5 Career Inflection Points

Built for Specific Career Inflection Points, Not Generic Advice.

My practice at BreakthroughCareerCoaching.com is built around five career crossroads where upgrading your commercial and AI operating system transforms your trajectory.

01 · Early Tech Sales 02 · Consultative Sellers 03 · Career Pivoters 04 · GTM & AI Era 05 · Persona Mapping
Scenario 01 · Years 0 to 5

The Early Tech Sales Professional

For SDRs, BDRs, and Junior AEs shifting from high-volume script pitching to consultative deal execution.

✕ Where You Feel Stuck

  • Hitting quota relies on sheer volume and long hours, risking burnout.
  • Discovery calls stall as soon as prospects ask for "a one-pager."
  • Struggling to bypass gatekeepers or defend price without discounting.

✓ What We Master Together

  • Diagnostic Discovery: Incisive questions that position you as a trusted advisor.
  • Multi-Threaded Deals: Map champions and economic buyers so deals never stall.
  • Mutual Action Plans: Create natural deal urgency without high-pressure tactics.
Coaching Focus & Outcome

Shorter sales cycles, larger deal sizes, and consistent quota attainment.

Work With Me on Tech Sales →
Scenario 02 · Senior IC Sellers

The Consultative Seller Elevating Their Craft

For experienced B2B, media, agency, and enterprise sellers scaling from mid-market deals to $1M+ board-level partnerships.

✕ Where You Feel Stuck

  • CFO scrutiny and procurement pushback are compressing margins at renewal.
  • Plateaued at $20k–$80k deals without a playbook for $250k–$1M+ commitments.
  • Struggling to turn transactional renewals into multi-year partnerships.

✓ What We Master Together

  • Joint Business Plans (JBPs): Modeled on closing 16x $1M+ JBPs in a single year.
  • Asymmetric Negotiation: Trade strategic value instead of discounting margin.
  • CFO-Ready Business Cases: ROI narratives that executive boards approve first pass.
Coaching Focus & Outcome

Enterprise $1M+ deal mastery, stronger margin defense, and C-suite authority.

Elevate My Consultative Craft →
Scenario 03 · Career Inflection

The Career Pivoter (Into Tech or Sales → GTM)

For professionals breaking into tech or moving from quota sales into GTM Strategy, Product Lead, or Operations.

✕ Where You Feel Stuck

  • Pigeonholed as "just a quota carrier" when applying for GTM or strategy roles.
  • Your CV lists sales targets instead of cross-functional strategic impact.
  • Stumbling in structured interviews when tested on leading without authority.

✓ What We Master Together

  • Executive CV Repositioning: Reframe your story around market scaling and GTM strategy.
  • Lead Without Authority: Shift from quarterly quota thinking to multi-year planning.
  • Scored Mock Interviews: Practice with a 200+ interview veteran. (Excludes Google roles.)
Coaching Focus & Outcome

A repositioned executive narrative and complete mastery of external tech hiring loops.

Plan My Career Pivot →
Scenario 04 · Applied AI Advantage

The GTM & Commercial Leader in the AI Era

For commercial, GTM, and marketing professionals ready to eliminate manual admin grind and lead internal AI adoption.

✕ Where You Feel Stuck

  • Overwhelmed by AI hype without practical workflows for daily GTM execution.
  • Still spending hours every week on repetitive research, reporting, and deck prep.
  • Struggling to prove measurable AI business impact to senior leadership.

✓ What We Master Together

  • Practical AI Brainstorming: Brainstorm practical AI workflows and concepts to cut down on repetitive administrative grind every week.
  • 2,000-Seller Enablement Playbook: Proven AI adoption models from Google EMEA.
  • Internal AI Leadership: Package your AI workflows into promotion-ready team assets.
Coaching Focus & Outcome

Practical AI concepts and workflow ideas to cut down on repetitive administrative grind and become more efficient every week.

Master AI-Native GTM →
Scenario 05 · Self-Discovery & Direction

Strategic Career & Persona Mapping

For mid-to-senior professionals seeking deeper self-awareness, strengths clarity, and long-term career direction.

✕ Where You Feel Stuck

  • Feeling plateaued or restless, unsure whether to switch companies, roles, or tracks.
  • Reacting opportunistically to recruiters instead of executing a multi-year plan.
  • Unclear on your distinct commercial persona and highest-leverage strengths.

✓ What We Master Together

  • Strengths & Persona Clarity: Uncover your core commercial strengths, blind spots, and highest-value operating style.
  • 3-Year Horizon Modeling: Compare three distinct career paths across ROI and fit.
  • Actionable Next-Step Planning: Translate long-term career goals into clear, practical priorities you can execute immediately.
Coaching Focus & Outcome

Clearer self-awareness around your commercial strengths and practical direction for your next career move.

Build My Career Blueprint →
Mutual Fit & Policy Boundaries

Who This Coaching Is NOT For

To protect client outcomes and comply strictly with Google employee conflict-of-interest policies at BreakthroughCareerCoaching.com, this program is not for:

✕ Google Interview Prep or Referrals

In strict adherence to Google employee policies, I do not provide interview coaching for roles at Google, discuss internal Google data/operations, or provide internal referrals to Google or any other company.

✕ Overnight Shortcuts

Those seeking superficial scripts rather than doing the deliberate work to build lasting commercial, GTM, and AI mastery.

✕ Passive Discussion

Those who enjoy career theory but won't execute agreed action plans or pre-session diagnostics between calls.

See Yourself in One of These Scenarios?

Apply below to diagnose your primary bottleneck, map your target trajectory, and confirm mutual fit.

Apply for 1-on-1 Coaching → View Packages & Pricing