stephenrogan
- 127 skills
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- 15 hours ago last updated
- ▌ Stakeholder Map Builder · stephenroganBuilds a structured map of customer stakeholders with roles, influence levels, engagement status, and relationship strategy per contact. Identifies coverage gaps and single-thread risk. Use when asked to map stakeholders, build an org chart, assess relationship coverage, identify single-thread risk, plan stakeholder engagement, or when a CSM needs to understand who matters at an account and where the relationship gaps are. Also triggers for questions about stakeholder mapping, contact assessment, org chart analysis, relationship coverage, multi-threading assessment, or who to engage at a customer account.
- ▌ Value Narrative Builder · stephenroganConstructs a compelling value narrative for a customer account by connecting product usage to business outcomes in the customer's language. Produces different versions for different audiences -- the champion, the CFO, the board. Use when asked to build a value story, articulate ROI, create a business case for the customer, prepare value evidence for a renewal or QBR, or when a CSM needs to translate usage metrics into business impact the customer will recognise. Also triggers for questions about value articulation, ROI storytelling, customer business case, value evidence, or how to prove the product is worth the investment.
- ▌ Account Strategy Builder · stephenroganDevelops a structured 90-day strategic plan for a key account by defining priorities, setting measurable objectives, mapping stakeholder strategy, and identifying risks and opportunities. Use when asked to build an account strategy, create an account plan, develop a strategic approach for a key account, set quarterly objectives for an account, or when moving from reactive account management to proactive strategic management. Also triggers for questions about account planning, strategic account management, quarterly account objectives, or how to develop a structured plan for a high-value customer.
- ▌ Customer Apology Crafter · stephenroganWrites genuine, non-corporate apologies after service failures, outages, missed commitments, or other situations where the customer was let down. Provides multiple framing options calibrated to the severity of the failure and the state of the relationship. Use when asked to write an apology email, draft a service failure response, compose a mea culpa, acknowledge a mistake to a customer, or when any situation requires a formal acknowledgement that something went wrong. Also triggers for questions about customer apologies, service recovery communications, trust repair, or handling a situation where the company made a mistake.
- ▌ Manual Health Assessment · stephenroganGuided diagnostic that scores account health through structured questions across five dimensions -- usage, engagement, support, sentiment, and commercial health. Produces a health classification with component breakdown and recommended actions. No automated data required -- the CSM's knowledge is the input. Use when asked to assess account health, evaluate a customer's risk level, score an account without a health scoring system, or when a CSM wants a structured way to evaluate where an account stands. Also triggers for questions about account risk, customer health, or portfolio assessment. The entry point to structured health thinking.
- ▌ Multi Threading Playbook · stephenroganProvides a structured approach to expanding relationships beyond a single contact at a customer account. Identifies target contacts, recommends engagement approaches, and builds a multi-threading strategy to reduce single-thread risk. Use when asked to multi-thread an account, expand relationships at a customer, reduce single-thread risk, build broader stakeholder coverage, develop new contacts, or when a CSM realises they are dependent on one person at a key account. Also triggers for questions about relationship breadth, single-thread risk, stakeholder expansion, going wide at an account, or how to build relationships with people beyond the primary contact.
- ▌ Business Review Framework · stephenroganProvides a lighter alternative to a full QBR for mid-market and SMB accounts that need value conversations but do not warrant a formal quarterly business review. Structures a 20-30 minute business check-in with usage highlights, value evidence, and forward-looking discussion. Use when asked to run a business review without a full QBR, structure a lighter customer review, build a mini-QBR, create a business check-in framework, or when an account needs a value conversation but a full QBR would be disproportionate to their size or complexity. Also triggers for questions about business review alternatives, scaled QBR formats, lightweight business reviews, or how to deliver value conversations to mid-market and SMB accounts efficiently.
- ▌ Change Management Advisor · stephenroganProvides a structured framework for helping customers drive internal adoption of your product within their organisation. Addresses resistance, stakeholder alignment, communication strategy, and phased rollout planning from the CSM's perspective as an external advisor. Use when asked to help a customer with change management, advise on internal adoption strategy, address resistance to product adoption, plan a team rollout, or when adoption is stalling not because of the product but because of the customer's organisational readiness. Also triggers for questions about customer change resistance, internal adoption blockers, rollout planning, or how to help customers get their teams to actually use the product.
- ▌ Contract Review Assistant · stephenroganWalks through a customer contract to identify key commercial terms, renewal conditions, pricing structure, auto-renewal clauses, termination requirements, and negotiation leverage points. Produces an annotated summary the CSM can use for renewal preparation. Use when asked to review a contract, identify key terms, find renewal clauses, understand pricing structure, prepare for a commercial negotiation, check termination conditions, or when a CSM needs to understand what the contract actually says before a renewal or expansion conversation. Also triggers for questions about contract terms, commercial conditions, pricing clauses, auto-renewal provisions, termination notice periods, or preparing for a contract negotiation.
- ▌ Executive Briefing Writer · stephenroganCondenses account context into structured executive summaries of varying depth -- from a 30-second verbal brief to a one-page written summary. Formats for the specific executive audience (your leadership, the customer's leadership, or both). Use when asked to prepare an executive briefing, write an account summary for leadership, create a board-level overview, condense account information for a VP or CRO, or when a CSM needs to brief someone senior quickly. Also triggers for questions about executive summaries, leadership briefings, account snapshots for management, or condensing complex account situations into executive-ready formats.
- ▌ Presentation Personaliser · stephenroganAdapts a generic presentation deck or template to a specific customer account by inserting relevant data, adjusting framing for the audience, and ensuring all references are account-specific. Use when asked to personalise a deck, customise a presentation for a specific customer, adapt a template for a meeting, tailor slides with account data, or when any generic presentation needs to be made specific before a customer interaction. Also triggers for questions about deck customisation, presentation personalisation, template adaptation, or making a generic deck feel account-specific.
- ▌ Stakeholder Research Prep · stephenroganPrepares structured background research on a customer contact before a first meeting or engagement. Builds a profile including likely priorities, role-specific concerns, engagement approach, and conversation starters based on their title, function, and seniority level. Use when asked to prepare for a first meeting with a new contact, research a stakeholder, build a contact profile, prepare for an executive conversation, or when meeting someone at a customer account for the first time. Also triggers for questions about stakeholder preparation, first meeting research, contact profiling, or executive meeting prep with someone you have not met before.
- ▌ Usage Pattern Interpreter · stephenroganTakes raw usage data -- even a spreadsheet export or pasted metrics -- and identifies patterns, risks, and opportunities. Translates product analytics into account intelligence a CSM can act on. Use when asked to interpret usage data, analyse product metrics, make sense of a usage report, identify trends in customer behaviour, flag usage-based risks, or when a CSM has data but does not know what it means for the account. Also triggers for questions about usage analysis, product analytics interpretation, behavioural pattern detection, usage-based risk identification, or turning raw metrics into actionable insight.
- ▌ Cs Investment Case Builder · stephenroganBuilds the business case for CS investment -- headcount, tooling, programmes, or operational improvements. Structures the argument in CFO-ready language with ROI projection, risk quantification, and evidence from portfolio data. Use when asked to build a business case for CS resources, justify headcount, make the case for a CS tool, propose a programme investment, or when a CS leader needs to secure budget or approval from finance or executive leadership. Also triggers for questions about CS headcount justification, tooling business cases, CS ROI for leadership, budget requests, or how to make the financial case for investing in customer success.
- ▌ Customer Sentiment Decoder · stephenroganInterprets mixed or contradictory signals from a customer by analysing the gap between what they say, what they do, and what the data shows. Produces a structured interpretation with investigation recommendations. Use when asked to decode customer sentiment, interpret mixed signals, make sense of contradictory behaviour, assess what a customer really thinks, or when a customer's words do not match their actions. Also triggers for questions about reading between the lines, interpreting customer behaviour, understanding contradictory signals, assessing true customer satisfaction, or when something feels off about an account but you cannot pinpoint why.
- ▌ Executive Outreach Drafter · stephenroganWrites the initial outreach email to a senior stakeholder the CSM has not engaged before -- going high for the first time. Calibrates register, framing, and approach to executive communication standards. Use when asked to write an email to a VP, CRO, CFO, or C-suite contact at a customer account, draft an executive outreach, compose a going-high email, engage a new senior stakeholder, or when the CSM needs to establish a relationship at a level above their primary contacts. Also triggers for questions about executive email drafting, going high strategy, senior stakeholder engagement, or first-time executive outreach.
- ▌ Quarterly Planning Builder · stephenroganHelps a CSM build their quarterly plan with portfolio priorities, measurable targets, focus areas, capacity allocation, and development goals. Produces a structured plan that can be shared with management and reviewed at quarter-end. Use when asked to build a quarterly plan, set Q1-Q4 goals, create a portfolio strategy for the quarter, plan the next 90 days, or when a CSM needs to move from reactive week-to-week management to proactive quarterly strategy. Also triggers for questions about quarterly planning, goal setting for a period, portfolio prioritisation for the quarter, or structuring a 90-day plan.
- ▌ Re Engagement Email Writer · stephenroganWrites outreach to customers who have gone dark -- not responded to recent communications, missed meetings, or disengaged from the product. Differs from a check-in email by acknowledging the silence and offering a specific reason to re-engage rather than asking if everything is fine. Use when asked to write a re-engagement email, reach out to a silent customer, draft an outreach to a customer who has gone dark, break through to an unresponsive contact, or when a no-reply streak indicates the customer has disengaged. Also triggers for questions about customer silence, unresponsive accounts, re-engagement strategy, or breaking through communication barriers.
- ▌ Competitive Threat Assessor · stephenroganEvaluates the severity of a competitive threat on a specific account by assessing the evaluation stage, trigger, relationship strength, and switching cost. Produces a threat classification with a response framework. Use when asked to assess a competitive signal, evaluate a competitive threat, determine how serious a competitor situation is, prepare a competitive response, or when a customer has mentioned evaluating alternatives. Also triggers for questions about competitive analysis on a specific account, handling competitor mentions, responding to customer evaluations, or assessing the risk of losing an account to a competitor.
- ▌ Renewal Conversation Opener · stephenroganFrames the initial renewal conversation by leading with value delivered, transitioning to forward-looking partnership, and anticipating likely objections based on account context. Produces multiple opening approaches calibrated to the account's health, relationship, and commercial situation. Use when asked to prepare for a renewal discussion, draft a renewal email, frame a renewal conversation, open a retention dialogue, or when a CSM needs to move from relationship management to commercial conversation. Also triggers for questions about renewal preparation, retention conversation strategy, renewal email drafting, or how to start the renewal discussion with a customer.
- ▌ Expansion Opportunity Scorer · stephenroganScores expansion readiness for a customer account by assessing adoption depth, value realisation, stakeholder alignment, commercial signals, and timing. Produces a readiness classification with the recommended expansion approach and the specific signal that triggered the assessment. Use when asked to assess expansion potential, evaluate upsell readiness, score an account for growth, determine whether a customer is ready for a commercial conversation about expansion, or when a CSM detects expansion signals and needs to decide whether and how to pursue them. Also triggers for questions about expansion timing, upsell assessment, growth readiness, when to start an expansion conversation, or evaluating whether a customer is ready to buy more.
- ▌ Territory Transition Planner · stephenroganBuilds a structured 30-60-90 day plan for a CSM taking over a new book of accounts or joining a new team. Prioritises accounts by risk and value, identifies immediate relationship actions, and structures the ramp to full productivity. Use when asked to plan a book transition, create a new CSM onboarding plan, structure a territory takeover, build a 30-60-90 plan for a new role, or when a CSM is inheriting accounts and needs a systematic approach to getting up to speed. Also triggers for questions about account transitions, new book ramp-up, CSM onboarding to a portfolio, territory planning, or how to take over accounts from another CSM.
- ▌ Escalation Decision Framework · stephenroganHelps a CSM decide whether to escalate an issue, when to escalate, to whom, at what severity, and how to frame it. Distinct from the escalation-brief-writer (which structures the escalation document) -- this skill helps with the judgment call of whether escalation is the right move. Use when asked to decide whether to escalate, determine the right escalation level, assess whether an issue warrants internal attention beyond the CSM, or when a CSM is unsure whether a customer issue is "bad enough" to escalate. Also triggers for questions about escalation judgment, severity assessment, when to involve leadership, whether to escalate or handle it yourself, or how to decide the right escalation level.
- ▌ Executive Engagement Playbook · stephenroganFramework for when and how to involve executives -- yours and the customer's -- in the account relationship. Covers timing, framing, preparation, and follow-through for executive engagement at renewal, expansion, escalation, and strategic alignment points. Use when asked about executive engagement strategy, when to go high, how to involve leadership, how to prepare for an executive meeting, or when a situation warrants moving beyond the CSM-level relationship. Also triggers for questions about executive sponsorship, VP-level engagement, C-suite involvement, strategic account elevation, or when leadership involvement could unlock an outcome the CSM cannot achieve alone.
- ▌ Internal Status Update Writer · stephenroganCompiles account portfolio status into formatted internal updates for leadership, cross-functional teams, or manager reviews. Adapts detail and framing by audience. Use when asked to write a status update, compile a portfolio summary for leadership, create a weekly report for your manager, draft a cross-functional update on key accounts, or when any internal audience needs a structured view of account status. Also triggers for questions about internal reporting, portfolio status updates, manager updates, leadership summaries, or how to communicate account status to internal stakeholders.
- ▌ Difficult Conversation Drafter · stephenroganPrepares talking points and framing for difficult customer conversations including delivering bad news, addressing underperformance, raising pricing concerns, discussing missed commitments, or having an honest conversation about a failing relationship. Use when asked to prepare for a difficult conversation, frame bad news, plan a confrontational discussion, structure a hard conversation, or when a CSM knows a conversation will be uncomfortable and needs to prepare how to navigate it. Also triggers for questions about hard conversations, delivering bad news to customers, uncomfortable customer topics, or how to raise a difficult subject without damaging the relationship.
- ▌ Pricing Conversation Framework · stephenroganStructures pricing discussions with customers including renewal pricing, discount requests, price increases, and competitive pricing pressure. Provides frameworks for leading with value, handling objections, and knowing when to concede versus when to hold. Use when asked to prepare for a pricing conversation, handle a discount request, communicate a price increase, respond to competitive pricing, or when any commercial discussion involves pricing. Also triggers for questions about pricing strategy, discount negotiation, price increase communication, commercial conversations, or handling the "it is too expensive" objection.