Head of Customer Success

Company Overview

Located in London with a hybrid work model requiring 2-3 days in the office weekly, trumpet is a dynamic and diverse company working to revolutionize sales and go-to-market (GTM) strategies. Supporting over 7,500 clients such as HubSpot and Gong, trumpet provides digital sales rooms enriched with AI-driven insights to accelerate sales cycles and streamline buyer journeys. Backed by top investors and having raised $9 million, trumpet is expanding rapidly and focuses heavily on building strong, cross-functional teams.

Role Summary

The Head of Customer Success will lead trumpet's Customer Success organization, reporting directly to the CEO and CRO. This is a hands-on leadership position tasked with managing the entire post-sale customer journey—from onboarding and adoption to support, renewal, expansion, and churn prevention. You will inherit a seasoned and award-winning team and drive the evolution of Customer Success into a repeatable growth engine internationally.

Key Responsibilities

• Oversee Customer Success metrics including gross retention rate (GRR), net retention rate (NRR), churn rates, renewal and expansion annual recurring revenue (ARR), adoption, and forecast accuracy.
• Lead and develop a multi-disciplinary team comprising Customer Success Managers, Onboarding, Digital CS, and CS Operations specialists.
• Mentor CSMs to conduct outcome-driven conversations with commercial confidence, engaging senior stakeholders effectively and managing renewal and expansion opportunities.
• Design clear customer segmentation strategies with targeted motions for high-touch, enterprise, mid-market, and scaled digital customers.
• Develop lifecycle playbooks covering all stages from onboarding to churn prevention and advocacy, alongside persona-specific playbooks using the C.A.R.E.S. stakeholder model.
• Enhance renewal forecasting accuracy and initiate proactive risk management to identify churn risks well before renewal discussions.
• Implement repeatable expansion processes empowering CSMs to recognize value and commercial opportunities and collaborate with sales leadership on pricing and packaging.
• Serve as executive sponsor on critical accounts, participating in key customer meetings, renewals, and expansion negotiations.
• Manage the customer support function through CS operations, focusing on support tools, service quality, knowledge bases, and customer escalations.
• Refine the Customer Success operating system utilizing tools like HubSpot, Sequence, Equals, and Intercom to optimize workflows, reporting, and automation.
• Ensure leadership trusts customer health dashboards, signals, reporting, and forecasts by enhancing visibility and cadence.
• Function as the internal voice of the customer, distilling insights for product roadmap influence and strategy alignment within cross-functional teams.
• Maintain and nurture team culture with clear expectations, performance standards, and career progression frameworks.

Performance Metrics

• Customer Success recognized as a growth driver with ownership of retention, renewals, and expansion.
• Continual improvement in GRR, NRR, churn, expansion ARR, adoption rates, and forecast precision.
• Effective segmentation with tailored customer engagement models and comprehensive playbooks for all lifecycle stages.
• CSMs mature into strategic, commercially savvy professionals skilled in executive engagement and negotiation.
• Early risk detection mechanisms reduce churn and renewal disruptions.
• Predictable and proactive renewal and expansion processes.
• Successful scaling of the Digital Customer Success model for lower ARR clients.
• High-quality, connected customer support aligned with broader customer lifecycle.
• Influential customer feedback driving product development and growth strategies.
• A motivated, developed, and proud Customer Success team.

Required Experience

• Track record leading Customer Success teams of similar size in B2B SaaS, directly managing at least six CSMs.
• Expertise in managing commercial post-sale KPIs such as renewal rates, retention, churn prevention, expansion, and forecasting.
• Experience with mid-market and complex enterprise customer environments.
• Demonstrated ability to build or enhance Customer Success frameworks, including segmentation and lifecycle playbooks.
• Skilled coach for developing CSMs into strategic and executive-ready advisors.
• Proven capacity to act as executive sponsor in high-impact client engagements.
• Strong knowledge of customer health indicators, churn risk management, and proactive account strategies.
• Collaborative approach to working with Sales on expansion, negotiations, and growth planning.
• Experience developing scalable digital and tech-driven Customer Success motions.
• Strong operational skills managing tools, data, workflows, and reporting solutions.
• A hands-on leader comfortable in fast-paced environments, balancing process improvements and close customer interactions.
• Excellent at communicating complex business and product concepts to varied audiences.

Preferred Qualifications

• Background in SaaS companies serving Sales, GTM, Revenue Operations, Enablement, or customer-focused teams.
• Experience managing or collaborating with CS Ops, Support, onboarding, or implementation teams.
• Familiarity with HubSpot, Sequence, Equals, Intercom, PostHog, and other CS tooling.
• Experience guiding a company's scale-up from mid-market to enterprise-level customers.
• Proven ability to establish voice-of-customer programs and influence product roadmaps.
• Knowledge of stakeholder mapping, multi-threaded account strategies, and MEDDPICC methodologies.
• Experience in high-growth startup or scale-up environments developing scalable processes.

Company Values

• Relentless ambition to grow.
• Customer obsession.
• Trust, respect, and care for colleagues.
• Bold innovation and risk-taking.
• A culture of feedback.
• Data-driven inspiration and decision-making.

Interview Process

• Initial 30-minute screening.
• In-depth interview.
• Practical exercise (details to be confirmed).
• Values-based interview.

Benefits

• £500 annual personal learning and development fund.
• 33 days of holiday including bank holidays.
• Pension through salary sacrifice with Penfold.
• Monthly wellbeing allowance (£45) via Juno.
• Top-tier equipment provision (laptop, monitor, mouse, keyboard).
• Half day off on birthday.
• Enhanced sick pay (10 days).
• Improved maternity and paternity leave policies.
• Access to therapy sessions through Pebble Therapy.
• Regular office lunches every two weeks.
• Technology purchase scheme.