B2B GTM Strategist for an Engineering Leadership Coaching Business

TITLE: B2B GTM Strategist for an Engineering Leadership Coaching Business ABOUT THE BUSINESS The 3 Guarantees is a six-week applied coaching program for engineering managers. It helps managers shift from being the person who personally holds execution together to becoming the architect of a team that can deliver predictably, grow talent and maintain healthy systems. The program is organised around three outcomes: * Predictable Delivery * Talent Multiplication * System Health The participant-facing proposition is simple: “I show engineering managers what the job really is.” The program has been delivered successfully to three participants, with strong testimonials. I’m Chirantan Rajhans, the founder. I bring 19 years of experience in software engineering, including 10 years in engineering management. The business is now moving towards an organisation-sponsored B2B model, in which VPs, Directors, CTOs and Heads of Engineering may fund pilots or cohorts for their managers. THE ASSIGNMENT I’m looking for a senior B2B marketer to help determine how The 3 Guarantees should be positioned, packaged and taken to market for organisational buyers. This is not a request to execute a predetermined marketing process. I expect you to bring judgment and pattern recognition from relevant prior work, challenge my assumptions, determine what work is genuinely necessary and recommend the most effective route to the desired commercial outcomes. This is not exactly a conventional consultancy, training course or SaaS product. The immediate product is manager development, but the organisational buyer is ultimately purchasing improved engineering performance: stronger management capacity, more predictable execution, healthier delegation and teams that are less dependent on individual managers holding everything together. Experience selling or marketing engineering services, technical consulting or comparable expertise-led B2B services is therefore particularly important. QUESTIONS THE ENGAGEMENT SHOULD RESOLVE * Who is the most promising initial organisational buyer, and in what context? * What event or condition makes the problem urgent enough to act on? * What does the buyer believe they are purchasing: manager development, engineering performance, execution resilience, leadership capacity or something else? * How should the participant transformation be translated into an organisational value proposition without making inflated promises? * How should an initial organisational engagement, pilot or cohort be packaged and priced? * Which messages are most likely to earn attention and generate qualified conversations? * Which acquisition motions best fit the business’s stage, founder strengths and target market? * What evidence and commercial signals should guide subsequent investment? The exact approach is yours to propose. I do not expect research or process for its own sake. Relevant experience should allow you to form stronger hypotheses, accelerate the work and avoid unnecessary activities. DEFINITION OF DONE At the end of the engagement, I should have: 1. A clear initial market choice * A prioritised economic buyer and organisational context * A definition of the buying trigger, not merely a demographic persona * A reason for pursuing this segment before plausible alternatives * Clarity about which segments or use cases should not be prioritised yet 2. A coherent B2B position * A sponsor-facing value proposition connecting manager development to engineering performance * A clear bridge between the organisational buyer’s narrative and the participant-facing narrative * Differentiation from internal training, generic leadership coaching, online courses, mentoring and management consulting * A credible proof and objection framework 3. A sellable organisational offer * A recommended structure for the initial organisational engagement, pilot or cohort * Clear scope, buyer expectations, participant experience and intended observable outcomes * Pricing and commercial-packaging recommendations * A credible call to action and buying path 4. A prioritised acquisition strategy * A small number of acquisition motions ranked by expected fit and learning value * An explanation of why these motions suit the business * Clarity about what has deliberately been deprioritised * Clarity about my role as founder and what should or should not be delegated * Practical success signals and stopping conditions 5. Usable commercial messaging The minimum set of messaging and sales assets needed to execute the recommended strategy. Depending on your approach, this may include: * A core sponsor narrative and messaging architecture * Organisational landing-page or one-page offer copy * Warm-introduction, partnership or targeted-outreach messaging * A discovery-conversation narrative * Responses to important buyer objections I am not looking for collateral for its own sake. Every asset should serve a specific role in the buying journey. 6. A decision-ready execution plan * Clear priorities for the following 90 days * Material assumptions, risks and unanswered questions * Measures of qualified demand and commercial progress * Decision points for continuing, changing or stopping each motion * A recommendation about what capability should be hired or outsourced next, if any 7. Transfer of reasoning I should understand not only your recommendations, but the commercial reasoning behind them. The engagement should leave me better able to interpret market feedback and make future GTM decisions independently. If you believe any of these outcomes are unnecessary, premature or incorrectly framed, I welcome that judgment. Explain what reasoning or evidence replaces them. REQUIRED EXPERIENCE Please apply only if you have personally helped sell or market engineering services, technical consulting or closely comparable B2B professional services. Relevant experience could include: * Software-development or engineering consultancies * Engineering-performance or technical-transformation consulting * Fractional CTO or VP Engineering services * DevOps, platform, reliability, data or architecture consulting * Specialist professional services where expertise and organisational outcomes are the product Strong candidates will have: * Personally led B2B positioning, messaging or go-to-market work * Marketed or sold to CTOs, VPs of Engineering, Directors of Engineering, Heads of Engineering or technology founders * Turned complex, intangible expertise into an offer an organisational buyer could understand and fund * Worked with an early-stage, founder-led business without a dedicated marketing department * Connected positioning and messaging to an actual acquisition and sales motion * Evidence of making deliberate market choices rather than producing broad strategy * The seniority to perform the work directly Additional useful experience includes: * Management development, professional coaching or cohort-based programs * Selling to US, UK or European technology organisations * Founder-led sales, referrals, partnerships, account-based prospecting or carefully targeted outbound * Familiarity with European and German direct-marketing constraints THIS IS NOT A FIT FOR * Generic digital-marketing agencies * Social-media managers or content-calendar providers * SEO or paid-advertising specialists without positioning experience * Lead-list vendors * Appointment-setting agencies * Bulk cold-email operations * Agencies where a senior person sells the engagement and juniors perform the work * Consultants who primarily deliver polished strategy decks without usable commercial decisions HOW TO APPLY Begin your proposal with this exact sentence: “The buyer is not the participant.” This is an attention check. Proposals that do not begin with that sentence will not be considered. Then answer the following questions directly: 1. What is the closest comparable engagement you have personally worked on? Explain: * What service was being sold * Who the economic buyer was * The commercial problem at the start * Your exact role * The most important strategic choice you made * The commercial outcome or learning 2. What experience do you have selling or marketing engineering services or technical consulting? Please be specific. Name the type of service, buyer and sales motion. If client confidentiality prevents naming the company, an anonymised but concrete description is acceptable. 3. What made the buyer act? Describe the organisational trigger, commercial urgency or internal problem that created demand in one relevant engagement. 4. What would your prior experience allow you to accelerate or avoid in this assignment? I’m interested in your pattern recognition, not your ability to repeat a standard methodology. 5. Based only on this brief, what are two assumptions you would want to examine before recommending an acquisition strategy? This is not a request for unpaid speculative strategy. I’m looking at how you distinguish an assumption from a conclusion. 6. What is one marketing activity you would probably not recommend at this stage, and why? 7. Who will personally perform the work? If you represent an agency, identify the individual who would do the strategic work and describe their relevant experience. Undisclosed subcontracting or junior handoffs are not acceptable. 8. Provide links to up to two relevant case studies, portfolio examples or redacted work samples. Please state what you personally contributed. Do not claim team results as individual work without explaining your role. 9. Provide your proposed fixed project fee, major milestones and availability. 10. State whether a reference from a comparable client would be available if you are shortlisted. Please do not include private contact information in the initial proposal. Generic pitches, agency brochures and unrelated portfolios will be rejected. Using AI to organise your proposal is fine; using it to manufacture vague experience is not. Please keep all initial communication on Upwork. I am not asking for unpaid finished strategy, creative work or a free consulting session.