Senior Scaled Customer Success Manager – Driving Adoption, Retention, and Growth for High‑Volume SMB Accounts at skillspath

About Skillspath

Skillspath is at the forefront of the legal technology revolution, delivering a cutting‑edge AI suite that empowers commercial lawyers to work faster, smarter, and more efficiently. Trusted by over 3,000 law firms and in‑house legal teams worldwide, we have scaled more than 25× since our launch in 2022. Our flagship product is used by industry leaders such as Nestlé, Fender, Crocs, and Securitas, and we are continuously expanding our portfolio of clients who rely on skillspath to streamline complex legal workflows and unlock new levels of productivity. If you are passionate about technology, law, and customer success, skillspath offers a unique opportunity to shape the future of legal services while working with a dynamic, high‑growth team.

Role Overview

We are seeking a highly organized, proactive, and creative Scaled Customer Success Manager (CSM) to lead adoption, retention, and engagement across a high‑volume portfolio of small to mid‑size customers. This role is perfect for someone who thrives on scale, excels at creative outreach, and can deliver measurable value without relying on frequent synchronous meetings. As a key member of our scaled success motion, you will blend automation, data insights, and human touch to drive exceptional outcomes for our customers and the business.

Key Responsibilities

• Portfolio Ownership: Manage a large portfolio of 100+ accounts, ensuring strong retention and product adoption at scale.
• Customer Onboarding & Training: Deliver 1:1 training calls and group sessions to help new and existing customers hit the ground running.
• Proactive Outreach: Conduct regular phone or Zoom check‑ins, and use targeted re‑engagement campaigns to keep customers engaged.
• Data‑Driven Risk Management: Monitor product usage across your portfolio, trigger automated alerts, and intervene early with at‑risk accounts.
• Creative Value Delivery: Use Loom videos, email playbooks, personalized content, and group training to provide value without relying on live meetings.
• ROI Articulation: Clearly communicate the ROI of skillspath and coach customers on under‑utilized features that improve efficiency and accuracy.
• Renewal Management: Own renewal conversations, showcasing usage, outcomes, and opportunities for further value, even with hard‑to‑reach customers.
• Cross‑Functional Collaboration: Partner with marketing, product, and CS leadership to refine scaled engagement strategies, playbooks, and automation flows.
• Data Hygiene & Reporting: Maintain accurate records in HubSpot, refine tracked success metrics, and contribute to health score improvements.

Essential Qualifications

• Minimum 2 years of experience in customer success, account management, or a similar role within a B2B SaaS environment.
• Proven track record managing high‑volume SMB customer segments with a focus on adoption and retention.
• Strong written communication skills – ability to craft persuasive emails, compelling product updates, and clear usage follow‑ups.
• Excellent organizational skills and a systems mindset; adept at refining workflows, segmenting accounts, and optimizing processes.
• Ability to identify churn risks through product signals and take proactive steps to turn the account around.
• Comfortable driving value without relying on live meetings – skilled at selling product worth through content, automation, and strategic outreach.
• Familiarity with CRMs (e.g., HubSpot) and a commitment to maintaining clean, consistent data hygiene.
• Self‑starter who thrives in a fast‑paced, constantly evolving environment.

Preferred Qualifications

• Experience with tools such as Mixpanel, Intercom, or customer success platforms like Vitally or ChurnZero.
• Background in legal tech or SaaS supporting professional services teams (legal, finance, consulting).
• Knowledge of AI‑powered legal solutions and the broader legal services market.

Core Skills & Competencies

• Customer‑Centric Mindset: Deep empathy for client challenges and a passion for delivering tangible outcomes.
• Analytical Thinking: Ability to interpret usage data, identify trends, and translate insights into actionable plans.
• Strategic Outreach: Creativity in designing scalable outreach programs that resonate with diverse audiences.
• Project Management: Strong ability to juggle multiple priorities, meet deadlines, and coordinate cross‑functional initiatives.
• Communication: Clear, concise, and persuasive written and verbal communication skills.
• Adaptability: Comfortable navigating ambiguity and pivoting strategies in a rapidly changing environment.

Career Growth & Learning Opportunities

At skillspath, your growth is a top priority. As a Scaled CSM, you will have the chance to:

• Lead the design and execution of enterprise‑scale success programs that shape the future of our customer experience.
• Collaborate with product, marketing, and engineering teams to influence roadmap decisions based on real‑world customer feedback.
• Mentor junior CSMs and contribute to the development of best practices across the organization.
• Earn a seat at the executive table as you demonstrate impact on revenue, churn, and customer satisfaction.
• Participate in ongoing learning initiatives, including industry conferences, AI workshops, and internal knowledge‑sharing sessions.

Work Environment & Culture at Skillspath

Skillspath is built on a foundation of autonomy, accountability, and outcome‑driven performance. Our culture is defined by:

• Remote‑First Flexibility: Work from anywhere while staying connected through collaborative tools and regular virtual huddles.
• Outcome Focus: We trust you to determine how to achieve results, not how to perform tasks.
• Inclusive Community: A diverse, supportive team that values every voice and fosters belonging.
• Continuous Feedback: Regular one‑on‑ones, peer reviews, and transparent metrics keep everyone aligned and growing.
• Well‑Being Commitment: We prioritize mental and physical health through wellness programs, flexible time off, and supportive policies.

Compensation, Perks, and Benefits

While specific figures vary by experience and location, skillspath offers a competitive total rewards package that includes:

• Base salary commensurate with market standards for senior CSM roles.
• Performance‑based bonuses tied to adoption, retention, and renewal metrics.
• Equity grants that give you a stake in skillspath’s long‑term success.
• Comprehensive health, dental, and vision insurance for you and your family.
• Generous paid time off, including holiday closures and flexible vacation policies.
• Monthly paid meals and an annual wellness allowance to support your well‑being.
• Parental leave top‑ups and family‑friendly benefits to support your growing family.
• Access to mental health resources, including a $1,000 stipend for therapy or counseling.

Why Join Skillspath?

Joining skillspath means becoming part of a mission‑driven team that is redefining legal services through AI. You will:

• Drive measurable impact on thousands of legal professionals worldwide.
• Work alongside passionate, high‑performing colleagues who value innovation and collaboration.
• Own a portfolio that challenges you to think strategically and act creatively.
• Benefit from a culture that rewards autonomy, accountability, and continuous learning.
• Secure a meaningful stake in a company poised for exponential growth.

How to Apply

If you are ready to take your customer success career to the next level and help legal professionals unlock the power of AI, we would love to hear from you. Submit your application through the link below, and let’s explore how you can contribute to skillspath’s success story.

Apply to this job

Skillspath is committed to creating an inclusive and supportive candidate experience. If you require any accommodation during the interview process, please let us know without hesitation.

Skillspath is an equal opportunity employer. We celebrate diversity and are dedicated to fostering an environment where all employees can thrive.