Strategic Customer Success Manager

About us

Insightful is a market-leading platform for employee productivity and workforce analytics. We process really big data, synthesize it into actionable insights and ultimately provide a best-in-class/easy-to use product which empowers enterprise customers to improve employee productivity, business processes and overall staff well-being.

Job Description

This role owns a concentrated portfolio of Insightful's most strategically important enterprise accounts, acting as the senior relationship holder for each one. The work is depth over volume: understanding each customer's business well enough to speak the language their leadership uses, building relationships that run from end users up to the C-suite, and building a tailored success plan per account rather than working from a standard cadence.

It reports to the Head of Customer Success and works closely with Product, Sales, and Support.

Responsibilities:

• Own a concentrated portfolio of Insightful's highest-value accounts as the senior strategic relationship holder — accountable for retention, health, and the long-term trajectory of each account
• Build and maintain deliberate, multi-threaded relationships across every strategic account, developing meaningful points of contact at the executive, operational, and end-user level so that no relationship hinges on a single stakeholder
• Operate with a C-suite and VP-level presence within each account; own the executive relationship, lead senior business reviews, and hold the kind of credibility that earns access to strategic conversations — not just renewal calls
• Deeply understand each customer's business: their organizational priorities, growth plans, workforce challenges, competitive environment, and the metrics their leadership uses to measure success; use that knowledge to position Insightful's value in the language their executives actually care about
• Identify and pursue value-add conversations opportunistically — reading signals across usage data, stakeholder feedback, business updates, and product roadmap to surface the right conversation at the right moment, whether that's a deeper use case, an untapped workflow, or an expansion that genuinely serves the customer's goals
• Lead bespoke, account-specific success planning — not templated cadences, but tailored roadmaps built around each customer's business objectives, maturity trajectory, and internal adoption dynamics
• Act as an early warning system for risk across the strategic book; connect the dots across stakeholder signals, usage trends, and commercial conversations to surface concerns before they become escalations, and own the resolution path when they do
• Partner closely with the Account Management team on commercial planning; CSM owns the health, depth, and strategic relationship — AM owns the commercial motion; the handoff between the two should be seamless and well-timed, driven by signals the CSM originates
• Translate Insightful's product roadmap into customer-specific value narratives; position upcoming capabilities in the context of each account's stated priorities and bring the right stakeholders into the conversation early
• Represent the strategic customer segment internally with specificity — bring forward product gaps, competitive intelligence, and use-case evolution in a way that influences roadmap decisions and cross-functional priorities
• Build customer advocacy across the strategic book; identify and develop reference customers, executive sponsors, and case study opportunities that reflect genuine mutual value
• Maintain meticulous account hygiene in Vitally and HubSpot — health scores, stakeholder maps, success plans, and activity logs should reflect real account state at all times, not just renewal-window snapshots
• Contribute to the development of strategic CS frameworks — EBR formats, executive engagement playbooks, stakeholder mapping templates — that raise the standard of engagement across the Premier tier
• Carrying out all other tasks as requested by leadership

You are a great fit for this role if you have:

• At least 6 years of experience in enterprise consulting, strategic account management, or customer success within B2B SaaS, including significant tenure managing complex, high-value portfolios.
• Proven ability to establish and maintain senior-tier partnerships, ensuring consistent impact and strategic sway with VP and C-level stakeholders at large organizations - particularly when they are not involved in the initial hand-off.
• Demonstrated expertise in building multi-threaded account relationships — navigating complex stakeholder environments to uncover engagement gaps and proactively expanding influence beyond the initial point of contact.
• Sharp commercial instincts – you know how to read a conversation for growth or risk signals, how to sequence a value-add discussion, and how to work hand-in-hand with an Account Management team without blurring the lines of ownership.
• Strong business acumen: you can speak the language of your customers’ leadership teams, connect Insightfuls’ value to their strategic priorities, and position the product in the context of real business outcomes.
• A proactive, anticipatory working style. You can identify risk and opportunity before they’re brought to you by the customer, and you take action without being asked, and without requiring input at every step .
• Excellent written and verbal communication: Clear, confident, and calibrated to the audience, whether that’s a Slack message to a day-to-day contact, or a prepared business review for a CEO.

How success is measured:

• Gross and net revenue retention across the strategic portfolio.
• Depth and stability of executive relationships — stakeholder map coverage, C-suite engagement cadence, and relationship continuity through customer-side turnover.
• Quality and consistency of success planning — bespoke account plans in place, current, and actually guiding engagement.
• Proactive opportunity identification: value-add conversations originated and routed to AM, expansion signals surfaced before renewal windows.
• Customer advocacy: reference accounts, case studies, and executive sponsor relationships developed within the portfolio.