Strategy & Operations, Customer Success

Job4Travelers; Boca Raton (FL); Remote; USD 110,000 - 145,000; Full time

Benefits offered by this job

Equipment budget

Education budget $100/month

Unlimited PTO (4 weeks recommended)

Stock option window 10 years

Job summary

Ashby is seeking a Strategy & Operations role within Customer Success. You will drive strategy, processes, and data-driven insights to improve customer health, retention, and revenue growth.

You’ll report to CS/Operations leadership and collaborate with Finance on planning cycles and headcount modeling. We value a self-starter with SaaS and financial literacy, strong data distillation skills, and the ability to work autonomously across multiple projects.

Qualifications

• Self-starter with curiosity and initiative.
• Strategic thinker able to distill data into actionable recommendations.
• Strong analytical skills for data-driven decisions.
• Experience with CRM reporting, preferably HubSpot.
• Comfort working autonomously across multiple initiatives.
• SaaS experience in fast-growth environments, CS or Revenue Ops ideal.

Responsibilities

• Operationalize CS strategy with scalable processes, tools, and workflows.
• Analyze metrics (NRR, GRR, churn, product adoption, health score, sentiment) and provide early warnings.
• Improve end-to-end customer journey from onboarding to renewal.
• Support strategic planning with headcount and capacity modeling insights.
• Drive process improvements across CS workflows, onboarding, transitions, and renewals.
• Define business requirements to improve CS efficiency and scalability with RevOps.

Skills

Self-starter

Analytical mindset

Strategic thinking

Data-driven recommendations

Excellent communicator

CRM reporting

HubSpot experience

Autonomous work style

Tools

HubSpot

Job description

CS Strategy & Ops Role at Ashby - Remote US/Canada — Remote

Remote Flexibility: Ashby hires across the US and Canada, and while no explicit timezone requirement is stated, a Customer Success Strategy & Operations role typically involves regular collaboration with CS leadership, Finance, and cross-functional teams. Expect some synchronous availability during US business hours (PT–ET), making this better suited to nomads in the Americas or early-morning Western Europe than Southeast Asia or East Asia.

Async Culture Signals: The role involves a lot of independent analysis, framework design, and reporting — tasks well-suited to async work. However, change management and cross-functional alignment duties suggest frequent live meetings. This is a hybrid async role, not fully async.

Visa Considerations: With hiring open to both the US and Canada, digital nomad visa options are limited within those regions. If you hold a US or Canadian work authorization, you're well-positioned. Non-residents should note this role appears to require residency in one of these two countries.

Travel-Friendly Perks:

• Generous equipment & software budget — great for setting up a mobile workstation
• $100/month education budget (conferences covered with approval) — potential travel perk
• Unlimited PTO (4 weeks recommended) — solid window for extended travel between projects

If you're a nomad based in Lisbon or Medellín without US/CA authorization, this role is likely out of reach geographically. Focus your search on roles explicitly open to EU or LATAM residents.

Role Overview

In this Strategy and Operations, Customer Success role, you will drive the strategy, processes, and data-driven insights that empower our Customer Success Team to deliver exceptional outcomes for our customers. Reporting to the Manager of Strategy and Operations, and partnering closely with Customer Success leadership, you will define strategies and execute improvements that optimize customer health, retention, and revenue growth.

Our Customer Success team is consistently praised by our customers for their deep expertise, responsiveness, and dedication—a testament to how much we Care Deeply About Customers, one of our core Operating Principles. As we continue to scale, it's critical that we preserve and enhance this high standard of customer care while ensuring our processes, tools, and insights evolve to support sustainable growth.

You will play a crucial role in our operations, including process improvements, planning, and reporting. This is both a strategic and tactical role in which you'll design frameworks and programs, uncover actionable insights, and create data-informed recommendations across our Customer Success functions.

Operationalize CS Strategy: Develop and refine processes, tools, and workflows to scale Customer Success operations. This includes customer segmentation, onboarding workflows, lifecycle mapping, and playbook development.

Analyze Business Dynamics: Partner with internal stakeholders on reporting & analysis of metrics such as NRR, GRR, churn, product adoption, health score, and customer sentiment. Use these insights to provide early warnings and refine CS strategies.

Optimize the Customer Journey: Enhance the end-to-end customer journey, ensuring smooth transitions across all post-sales touch points from onboarding through support and renewal.

Support Strategic Planning: Collaborate with Finance and CS leadership on planning cycles, including headcount planning, capacity modeling, and quota setting. Provide relevant historical data for informed decision making.

Drive Process Improvements: Identify inefficiencies and implement improvements to CS workflows, customer onboarding, account transitions, and renewal processes. Implement & deploy KPIs to measure performance against strategic initiatives.

Optimize CS Systems: Define the business requirements to improve Customer Success efficiency, efficacy, and scalability. Partner with RevOps teammates to implement changes to tools (CRM, health scoring platforms, etc).

Collaborate Cross-functionally: Ensure alignment with Sales, Product, and other teams to align resources with customer needs and forecasted growth.

Support Change Management: Lead the roll‑out and adoption of new processes or workflows to the CS team. Partner with Enablement on larger scale change programs.

You could be a great fit if you:

Are a self-starter, innately curious in your approach

Bring both SaaS & financial literacy, offering an informed perspective on CS benchmarks (e.g. ideal book sizes)

Have a strategic mindset, with the ability to distill data into actionable recommendations

Are detail-oriented and committed to data accuracy and process quality

Have experience in fast-growth SaaS environments, ideally in a Customer Success or Revenue Operations role

Are skilled in CRM reporting, with preference for HubSpot experience

Work autonomously, managing multiple tasks and deadlines effectively

Are an excellent communicator, both verbally and in writing

This role may not be a fit if:

You're unwilling to manage both high-level strategy and hands-on execution

You're uncomfortable with ambiguity and prefer structured, predefined assignments

You prefer focused work on a single project at a time

You prefer working within a single team rather than across multiple teams

Interview Process

Our interview process is thorough — we aim to ensure each person joining the team is the right fit for Ashby and will provide ample information to assess if Ashby is the right fit for you. The process for this role is as follows:

Recruiter Screen with Talent Acquisition Team — 30 minutes

Virtual Onsite — 90 minutes

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 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.

If you're in the US, top-notch health insurance for you and your dependents, with all premiums covered by us.

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.

Yes, Ashby is hiring for this role in both the US and Canada, and there is no mention of a required office location. The role appears to be fully remote, though some synchronous collaboration is expected given the cross-functional nature of the work.

Is this role fully remote? Yes, Ashby is hiring for this role in both the US and Canada, and there is no mention of a required office location. The role appears to be fully remote, though some synchronous collaboration is expected given the cross-functional nature of the work.

Ashby looks for candidates with experience in fast-growth SaaS environments, ideally in Customer Success or Revenue Operations. Proficiency in CRM reporting (HubSpot preferred), SaaS metrics (NRR, GRR, churn), and the ability to work autonomously across multiple initiatives are key requirements.

What experience is required for this Strategy and Operations, Customer Success role? Ashby looks for candidates with experience in fast-growth SaaS environments, ideally in Customer Success or Revenue Operations. Proficiency in CRM reporting (HubSpot preferred), SaaS metrics (NRR, GRR, churn), and the ability to work autonomously across multiple initiatives are key requirements.

The process consists of four stages: a 30-minute recruiter screen, a 45-minute hiring manager interview, a 45-minute challenge interview, and a 90-minute virtual onsite. The process is designed to assess mutual fit.

What does the interview process look like? The process consists of four stages: a 30-minute recruiter screen, a 45-minute hiring manager interview, a 45-minute challenge interview, and a 90-minute virtual onsite. The process is designed to assess mutual fit.

Benefits include unlimited PTO (4 weeks recommended), a 10-year stock option exercise window, 12 weeks of fully paid family leave (US), generous equipment and software budgets, a $100/month education budget, and fully covered health insurance premiums for US employees.

What benefits does Ashby offer for this role? Benefits include unlimited PTO (4 weeks recommended), a 10-year stock option exercise window, 12 weeks of fully paid family leave (US), generous equipment and software budgets, a $100/month education budget, and fully covered health insurance premiums for US employees.

Yes, Ashby has disclosed that it may use AI-driven tools to assist its recruitment team in screening, assessing, and selecting candidates for this position.

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