Senior Account Manager, Customer Success

Job Description

At Pencil, we are driving innovation in advertising technology through our state-of-the-art SaaS product, which harnesses Generative AI to redefine content creation. Our mission is to make AI the default in advertising without replacing creative people. To achieve this, we need to make sure that our technology isn’t just in the hands of big brands - we need to try to help small businesses and creative individuals too.

As a Senior Account Manager, Customer Success, you'll own the commercial and strategic health of Pencil's more complex accounts — the ones with layered stakeholders, higher stakes, or agency partners like OLIVER and Jellyfish in the mix. You'll work independently on the issues that matter most to the business, mentor newer CSPs, and help shape how the CSP function operates, not just execute within it. Clients experience you as the person who's always thinking a step ahead of them; internally, you're the person other CSPs and CSTs go to when an account gets complicated.

Candidates must be located on the East Coast and within the Eastern Time Zone.

Key responsibilities

Own the commercial and strategic health of a portfolio of higher-complexity or higher-stakes accounts, including those with agency partners sharing the account.

Independently resolve complex, cross-functional account issues, escalating only when something is genuinely outside your authority to fix.

Coordinate with agency-side Account Director counterparts so client, agency, and Pencil are aligned before key moments — QBRs, renewals, and joint client events.

Mentor and be a go-to resource for newer CSPs, reviewing their account plans and QBR narratives and helping them level up.

Identify and help build improvements to CSP processes, playbooks, and tooling that benefit accounts beyond your own portfolio.

Your background

5-9 years of experience in customer success, account management, or strategic client partnership roles, with a track record on complex or enterprise-adjacent accounts.

Agency experience is essential. Candidates must have experience managing 3–7 client accounts simultaneously, with strong organisational and account management skills.

Demonstrated experience coordinating multi-party account relationships, including agency or partner-side stakeholders.

Experience mentoring or informally leading other client-facing team members.

History of building or improving processes, playbooks, or documentation that other people relied on.

Strong executive-level communication skills — comfortable building and delivering a QBR narrative to senior client stakeholders.

You’ll Thrive Here If You…

You work closely with the wider business — you don't just improve your own accounts, you create processes others use too.

You're the person newer CSPs come to for advice, and you take that seriously.

You navigate multi-party relationships (client + agency + internal teams) without losing sight of who owns what.

You bring a forward-thinking, change-ready attitude — you don't expect the product or the playbook to stay static.

You champion Pencil's values in how you show up, not just what you deliver.

KPIs & Success Measures

Retention, renewal, and expansion performance across a higher-complexity portfolio.

Escalations and complex issues resolved independently, without requiring leadership intervention.

Effectiveness of agency-partner coordination — joint QBRs and client events run in lockstep, not as two separate vendors.

• Mentorship impact — visible improvement in the CSPs you support.
• Adoption of playbooks or process improvements you've driven across the wider CSP team.
• Client satisfaction / executive stakeholder confidence across your accounts.

Benefits

25 days PTO plus public holidays, although we operate a Flexible Time Off scheme

Health insurance / private medical cover

• Monthly stipend towards wellness, fitness, and learning and development
• Remote - work from anywhere in your home country

Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy

Flexible working hours