Director of Customer Success

PredictAP; Newton (MA); Remote; USD 150,000 - 230,000; Full time

Job summary

PredictAP is seeking a Customer Success leader to guide a growing team and refine processes that ensure successful product adoption, customer ROI, and long-term retention. You will own the customer experience post-sale and partner with senior leadership to scale a repeatable CS model across enterprise accounts.

You’ll personally engage with large customers, define differentiated engagement strategies, and build playbooks, dashboards and advocacy programs to drive renewal revenue and customer

Qualifications

• Led a CS team, built onboarding processes, playbooks, churn/risk assessment, activation and renewal ownership.
• Direct experience managing enterprise B2B SaaS relationships with multi-stakeholder accounts.
• Experience with CRE/real estate software (Yardi, MRI) is a plus.
• Strategic thinker with hands-on leadership.
• Excellent written and verbal communication; obsessed with customer delight.
• Experience in start-up and remote work preferred.
• Ability to drive cross-functional collaboration and executive engagement.

Responsibilities

• Lead CS team day-to-day and drive continuous improvement.
• Understand customers deeply; partner with sales; document ROI.
• Refine onboarding and activation processes to hit volumes and revenue.
• Own post-onboarding account management and renewal targets.
• Create customer advocates and develop case studies and references.
• Develop actionable playbooks for different customer types and setups.
• Engage with enterprise accounts and coach CSMs for multi-stakeholder success.

Skills

CS team leadership

Onboarding processes

Playbooks development

Churn/risk assessment

Activation & renewal goals

Enterprise B2B SaaS

Executive stakeholder management

Partnership management

Remote work experience

Start-up experience

Job description

The Position

PredictAP’s Customer Success team is responsible for delivering a winning customer engagement model designed to ensure successful product adoption, customer ROI and ultimately customer retention and expansion. There is already a team of 4 in place with documented processes and best practices, but we are always looking to improve and as we grow ensure that the way we manage customers to success is repeatable and scalable.

As the day-to-day manager of the CS function, you will work closely in partnership with senior management to set direction, refine processes and develop the team to deliver this industry leading engagement model. Internally you will be part of the extended leadership team and recognized as owning the customer experience post sale and being a go-to leader on all things customer. You will personally be engaged with our largest enterprise customers and will help define a differentiated approach to managing these important relationships.

Key responsibilities

• Lead the team day-to-day, with a focus on continuous improvement as a team and individually. Turn team learnings into team improvements, ensure consistency in approach and leaning in to show by doing as appropriate. Set priorities and help CSMs focus on critical work, identifying automation and tooling that will enable everyone to do their best work. Optimize cross-functional interaction and ensure alignment with overall company goals and CS team and approach.
• Support a culture of deeply understanding our customers, as a driver to everything we do from customer engagement to product development. This process starts with partnering with sales to understand customers’ existing processes, pain-points and goals for adopting PredictAP. Document business goals and ROI with customers such that prediction accuracy is not the only marker of success. Bring this knowledge back to the rest of the company in leadership meetings and internal discussions.
• Continue to refine a successful onboarding and activation process, that delivers the expected volumes and revenues from each customer contract in the initial months of engagement. The CS team is responsible for quarterbacking a process that you will help refine over time and that includes cross-functional involvement across technical setup, training, support and ongoing end-user engagement. Ensure PredictAP brings it’s A-game during this critical phase. We track activation metrics and a part of the CS variable compensation plan is tied to achieving early volume activation goals.
• Drive development of a more robust post-onboarding account management approach. Using an appropriate mix of proactive engagement strategies (written account plans, regular QBRs, value-added reporting) and risk identification tools designed to ensure we maximize value and minimize problems for our customers. You own the renewal process and are tasked with achieving the Company’s logo and revenue retention targets against which part of the variable compensation plan is targeted.
• Create a deep bench of customer advocates, willing and enthused to work with us to create content (case-studies, testimonials, reviews, etc.) that can be used as part of new business and customer adoption campaigns and be willing to act as customer references.
• Develop actionable playbooks to document these processes and clearly articulate the differentiated approaches required for different types of customers, technical setups etc. Support feedback loops that drive continuous improvement around these playbooks.
• Engage directly with key enterprise accounts, defining how our customer engagement approach needs to differ with these customers and coaching CSMs to be successful in these more complex multi-stakeholder scenarios. Pull in Exec leadership to build multi-layered relationships.

What you bring

• You’ve led a CS team, built onboarding processes, developed playbooks for different scenarios, deployed churn/risk assessment systems and owned activation and renewal goals
• Direct experience managing enterprise B2B SaaS relationships. Accounts with multiple stakeholders across finance, operations, and IT. You’ve run QBRs with senior finance leaders (CFO, Controller, VP Accounting) and handled renewals at that level. Partnership management experience is a plus.
• Real estate industry experience is a strong plus, especially with large commercial real estate owners, operators, or managers, or in proptech or fintech serving finance and accounting teams. Familiarity with AP workflows or CRE accounting systems (e.g., Yardi, MRI) will help you ramp quickly and earn credibility with our customers.
• A strategic thinker but with a player/coach mindset. You’ve shown clear leadership but enjoy rolling up your sleeves and getting stuff done.
• Excellent communicator with both strong written and verbal skills. You value quality, attention to detail and are obsessed with delighting customers.
• Goal oriented but flexible in your approach. You are collaborative and understand the difference between “owning the responsibility” and leveraging the full team’s capabilities to reach the right outcome.
• Experience in a start-up and remote work environment is preferred.

What we offer

• Competitive base salary plus variable compensation tied to retention and expansion; equity in a fast-growing, category-defining company.
• Comprehensive medical, dental, and vision coverage; 401(k); generous PTO and parental leave.
• Remote-first culture with in-person onsites
• Direct access to founders and senior leadership