Cover Letter — Senior Director of Enterprise Customer Success
Adam Roberts Indianapolis, USA | roberts.john.adam@gmail.com | +1 317 514 4713
Dear Hiring Team,
The Senior Director of Enterprise Customer Success role caught my attention for a specific reason: you’re looking for someone to lead Customer Success for Enterprise and Financial Services customers. That’s precisely where I’ve spent the last six years—building and leading CS for financial institutions navigating ESG and sustainability reporting at Clarity AI.
I know your Financial Services customers.
My clients are asset managers, asset owners, banks, and institutional investors managing $15 trillion in AUM. They operate in complex, regulated environments—SFDR, CSRD, ISSB, SEC climate disclosures. They have demanding multi-stakeholder structures, long sales cycles, and high expectations for strategic partnership.
I’ve built trusted relationships with CFOs, Chief Sustainability Officers, CROs, and Heads of Risk at these institutions. I understand how to deliver value in environments where compliance is table stakes and business transformation is the real goal.
With Workiva’s acquisition of Sustain.Life, your Financial Services customers are increasingly asking about ESG reporting. I can speak their language from day one.
I’ve delivered the results this role demands.
- 156% NRR and ≥139% NRR for four consecutive years—driven by white-glove partnership and proactive engagement
- Gross churn under 5%—through rigorous risk management and early intervention
- 110% of upsell target in Year 1 after leading a strategic transformation from account management to opportunity generation
- 100% OKR attainment for four years running, with 90% talent retention
I’ve also maintained a direct portfolio of $3.5M ARR while leading the team—so I understand what it means to execute at the account level while driving strategy across the organization.
I’ve built the engagement models you’re looking for.
Your job description mentions “Signature Experience” and “proactive, outcome-based engagement.” At Clarity AI, I designed our tiered service model from scratch, achieving a 4× improvement in priority-weighted CSAT. I built the workflows, training programs, and governance structures that enabled consistent delivery across our most complex accounts.
Last year, I led a CS transformation—new materials, new processes, new governance—that shifted our team toward value-based engagement and expansion focus. We changed how our CSMs think about their role, and it worked.
I’m ready to execute.
The Senior Director role emphasizes execution alongside strategy, and that’s where I thrive. I’ve built the processes, hired the teams, implemented the tools, and managed the accounts. I’ve been a player-coach for most of my career.
I’m also a strong partner to Sales. At Clarity AI, I’ve worked closely with two CROs on joint account planning, renewal strategy, and GTM execution. I understand that CS and Sales succeed together or not at all.
I’d welcome the chance to discuss how my experience can help Workiva deliver exceptional outcomes for your Enterprise and Financial Services customers.
Best regards, Adam Roberts