About the Role:
As an Enterprise Customer Success Manager (CSM) / Strategic Execution Lead at Cascade Strategy, you’ll play a pivotal role in helping our enterprise customers successfully execute their strategies using Cascade’s strategy-led performance platform.
This is a hybrid role, primarily focused on Customer Success, while also acting as a strategic implementation and execution partner to customers. In addition to driving adoption and long-term value, you will work closely with enterprise leaders to translate strategy into execution, advising on practical ways to operationalize their plans using Cascade.
Cascade is cutting-edge AI software, at the forefront of helping organizations use AI to run their business, execute strategy, and make better operational decisions. As such, this role is ideal for someone who enjoys working with modern technology, experimenting with new tools, and helping customers rethink how work gets done.
You will work closely with our COO, VP of Customer Services, CEO, and Founder, playing an important role in shaping how we deliver value to customers. This position sits at the intersection of strategy consulting, customer success, and operational execution, and is likely to grow and evolve quickly as the company scales.
You will partner with Strategic Account Managers/Executives (SAM/Es), implementation and technical specialists as part of a Dedicated Account Team (DAT), delivering tailored support based on the customer’s unique needs. As a trusted advisor, you will drive product adoption, renewals, and expansion while building deep, consultative relationships with senior leaders across enterprise organizations.
If you are a strategic thinker who thrives in a fast-paced startup environment and is passionate about helping customers achieve meaningful business outcomes, we encourage you to apply.
Key Responsibilities:
1. Implementation, Strategy Execution & Adoption:
The technical aspects of implementation will be handled by our Services team. Your role is to collaborate closely with them while focusing on the strategic and operational side of onboarding. You will help customers translate their strategic plans into clear execution frameworks inside Cascade, driving adoption, executive buy-in, and ensuring the overall experience aligns with the value they expect to achieve.
You will partner with the DAT team to ensure new enterprise customers achieve time-to-value quickly, ensuring a strong launch and laying the foundation for long-term success.
You will also serve as a strategic execution partner, advising customers on how to operationalize strategy, align teams, and use Cascade to support performance management and decision-making. Develop a deep understanding of the product and customer use cases, and work closely with the DAT to ensure project milestones are met and value delivery is achieved on schedule while navigating complex organizations and diverse stakeholder groups.
2. Account Management & Relationship Building:
Develop a deep understanding of each assigned enterprise account and execute a comprehensive strategy for customer retention, growth, and long-term partnership.
Serve as the primary point of contact for strategic discussions, ensuring alignment between Cascade’s capabilities and the customer’s business goals.
Build trusted relationships at the C-suite and executive level, while also supporting operational champions inside the organization to drive adoption and sustained engagement.
3. Renewals & Expansions:
Secure renewals by clearly demonstrating the ongoing value Cascade provides and identifying potential risks early.
Identify expansion opportunities within existing accounts, leveraging insights from customer usage and strategic priorities, while partnering with sales to close upsell and cross-sell opportunities.
4. Change Management & Strategy Support:
Guide customers through organizational and operational change, ensuring smooth adoption of Cascade across teams.
Provide thought leadership on strategy execution, performance management, and operational alignment, positioning Cascade as a trusted partner in helping organizations achieve their strategic objectives.
5. Internal Innovation, Automation & Process Improvement:
Cascade is building the future of AI-powered strategy execution, and this role is expected to actively contribute to how we deliver that value.
You will be encouraged to:
- Identify opportunities to standardize processes and improve delivery models
- Explore ways to use AI internally to increase efficiency and scale customer success
- Look for creative and unconventional approaches to delivering customer value
- Contribute to the evolution of our customer success playbook and operating model
You will work cross-functionally with Product, Sales, and Support teams to advocate for customer needs and ensure our product continues to evolve based on real customer outcomes.
The Ideal Candidate:
1. Client Relationship Management:
Strong ability to build and nurture deep, trusted relationships with enterprise clients, acting as a strategic partner rather than just a software vendor.
2. Strategic & Operational Thinking:
Comfortable working with executives to translate strategy into practical execution, helping organizations align teams, goals, and performance measurement.
3. Product & Technology Curiosity:
Demonstrated ability to quickly learn complex SaaS products and identify creative ways to use technology—including AI tools—to deliver greater value.
4. Enterprise Customer Success Expertise
Experience managing complex enterprise accounts with multi-threaded relationships and influencing decision-makers across large organizations.
5. Commercial Acumen
A results-oriented mindset with a strong understanding of revenue retention, expansion opportunities, and customer growth.
6. Exceptional Communication
Ability to craft customized agendas, deliver focused executive conversations, and synthesize complex ideas into clear, actionable insights.
7. Proactive Problem Solver
Resourceful and autonomous, capable of anticipating challenges and developing creative solutions to address customer needs.
8. Change Management Experience
Experience guiding organizations through change management processes and helping teams adopt new technologies and ways of working.
Experience:
- Minimum 5 years in Enterprise Customer Success, Strategy Consulting, or Account Management within a SaaS or technology company with ACV > $50K.
- Experience working in growth-stage or startup environments, ideally post-Series A, with the ability to operate in fast-moving, evolving organizations.
- Experience managing the full customer lifecycle, including onboarding, adoption, renewals, and expansion.
- Experience advising enterprise organizations on strategy execution, operational alignment, or change management is highly desirable.
Key Metrics of Success:
- Gross Revenue Retention (GRR)
- Net Revenue Retention (NRR)
- Time To Value/ Implementation Cycle Lengths
- Product Adoption & Usage
- Customer Health / Risk Distribution
- Customer Outcomes & Strategic Impact
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