Manager of Renewals - Small and Medium Businesses

Hi, I’m Alex, Head of Contract Management (Renewals) at Ashby. Our Contract Management team plays a critical role in helping customers navigate renewal and commercial conversations thoughtfully, strategically, and with a high degree of trust. We are building a team that takes pride in delivering exceptional customer experiences while also protecting the long-term health of the business, and I am excited to be hiring a Manager of Contract Management (Renewals) to help scale and evolve this function.

In this role, you’ll lead and develop a team of Startup Contract Managers responsible for guiding customers through renewals, pricing conversations, negotiations, and long-term partnership planning. A key part of this role is helping the team navigate increasingly complex commercial conversations while building scalable processes, operational rigor, and repeatable frameworks that elevate both the customer experience and the effectiveness of the Contract Management organization.

You’ll partner closely with leaders across Customer Success, Sales, RevOps, Product, Legal, Finance, and Support to help shape how Ashby approaches renewals and long-term customer growth as we continue to scale upmarket.

About the Role

As the Manager of Contract Management, you’ll lead a team of global Startup Contract Managers responsible for renewal strategy, customer retention, and commercial partnership management across Ashby’s customer base. You’ll act as a coach, operator, and strategic thought partner — helping the team grow their commercial acumen, negotiation capabilities, and customer judgment while also building scalable systems and processes that allow the organization to operate effectively at scale.

In this role, you will:

• Lead and coach a team of 6 Startup Contract Managers (4 in America and 2 in EMEA) responsible for renewals, contract negotiations, and commercial partnership conversations. These individuals do high volume, about 400-450+ annual contract renewals.

• Up-level team performance through thoughtful coaching, operational discipline, and skill development across negotiation strategy, forecasting, customer communication, and stakeholder management

• Help build scalable renewal processes, systems, and operational workflows that improve efficiency while preserving a high-touch customer experience

• Partner cross-functionally with Customer Success, Sales, Product, Finance, Legal, Support, and RevOps to align on customer strategy and commercial outcomes

• Drive consistency in renewal execution, forecasting accuracy, CRM hygiene, and pricing governance across the team

• Support the team in navigating complex negotiations involving procurement, legal, executive stakeholders, pricing transitions, and multi-product commercial conversations

• Translate successful negotiation strategies and customer patterns into repeatable frameworks, playbooks, and enablement materials for the broader organization

• Help shape the long-term vision and operational strategy for the Contract Management function as Ashby continues to scale

Role Requirements

Team Leadership & Coaching

You have experience leading and developing high-performing customer-facing teams in a B2B SaaS environment. You know how to foster a culture centered around empathy, accountability, creativity, and transparency, while helping individuals grow through thoughtful coaching and continuous feedback.

Commercial Acumen & Negotiation Strategy

You have deep experience managing or overseeing complex renewals, pricing conversations, and contract negotiations. You understand how to balance customer partnership with commercial integrity, and can coach teams through nuanced negotiation scenarios with confidence and sound judgment.

Renewal Strategy & Forecasting

You understand how to proactively manage renewal risk, expansion opportunities, forecasting accuracy, and long-term account planning. You bring structure and discipline to renewal operations while remaining adaptable in dynamic customer situations.

Operational Mindset

You have experience building or improving scalable systems, workflows, and processes that allow teams to operate effectively at scale. You value operational excellence, data accuracy, and thoughtful process design.

Cross-Functional Collaboration

You are comfortable partnering across Sales, Customer Success, Product, RevOps, Legal, Finance, and Support to align around customer needs, pricing strategy, and long-term business outcomes.

Customer & Executive Communication

You are an excellent communicator who can navigate challenging conversations with empathy, professionalism, and clarity. You know how to build trust with both customers and internal stakeholders while maintaining transparency throughout the renewal process.

Problem-Solving Orientation

You don’t rely solely on “what worked before.” You are thoughtful, adaptable, and solutions-oriented — able to navigate ambiguity and develop creative approaches to complex commercial challenges.

Data-Driven & Strategic

You are comfortable using data, trends, customer insights, and operational metrics to drive decision-making and improve both team performance and customer outcomes.

You’ll Be a Great Fit If You:

• You communicate with clarity and empathy. You ask thoughtful questions, simplify complex concepts, and build trust through transparent communication.

• You enjoy coaching. You see every negotiation, renewal, and customer interaction as an opportunity to help your team learn and grow.

• You are highly operational. You value strong internal systems, accurate forecasting, clean data, and scalable process design.

• You thrive in dynamic environments. You are energized by solving complex problems and adapting processes as the business evolves.

• You balance customer advocacy with business integrity. You can empathize deeply with customer needs while confidently protecting Ashby’s long-term commercial interests.

• You are a strategic problem solver. You know how to navigate ambiguity, identify creative solutions, and align multiple stakeholders toward a shared outcome.

• You enjoy building. You are excited about helping shape the future of the Contract Management organization and scaling its impact across Ashby.

You Might Not Be a Fit If:

• You prefer highly rigid, unchanging processes and environments.

• You are uncomfortable navigating pricing conversations, negotiations, or commercial ambiguity.

• You prefer operating independently rather than through cross-functional collaboration and team development.

• You are more interested in defining high-level strategy than owning execution alongside your team.

• You avoid operational detail, forecasting rigor, or system/process improvement work.

• You are uncomfortable balancing customer empathy with accountability and commercial discipline.

• You prefer transactional customer interactions over long-term strategic partnership building.

Our Philosophy

Here are a few key points (relevant to the go-to-market side) that should give you an idea of what it is like to work with us:

• We spend a lot of time building best-in-class products since we believe a highly differentiated product is easier to position and support in commercial conversations.

• We believe deeply in pairing customer empathy with accountability and operational excellence.

• We value thoughtful communication, principled decision-making, and strong ownership across every function.

• We strongly believe that small teams with very talented people deliver significantly better outcomes than large teams with unclear ownership or low accountability.

• We care deeply about helping customers succeed while also building a sustainable, scalable business.

We value a strong sense of ownership, principled thinking over experience, and thoughtful communication — we’ll get into these and other values throughout the interview process.

Interview Process

At Ashby, our interview process is designed to help you show your best self while also giving you insight into how we operate as a team. The process typically includes:

• Recruiter Screen - 30 minutes

• Hiring Manager Interview - 45 minutes

• Strategic Exercise - Take-home assignment

• Final Round - 2 hours

  • Rather than a traditional panel interview with a large group, we structure our panel into a series of smaller conversations. This gives you the opportunity to meet with multiple team members in a more conversational setting focused on specific topics, instead of a formal Q&A.

Benefits

• You’ll get the time to do things the right way; we put a lot of emphasis on high quality work and avoid quick hacks as much as possible.

• 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby - do it when you feel financially comfortable.

• Unlimited PTO with four weeks is recommended per year. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅

• Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise.

• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!

• $100/month education budget with more expensive items (like conferences) covered with manager approval.

  Ashby’s success hinges on hiring exceptional people and creating an environment where they can do their best work. We’re being intentional about building that environment from the ground up, and we hope that excites you enough to apply.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.