Middle 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 an Account Manager, Customer Success, you'll own the commercial and strategic health of a portfolio of Pencil accounts — the roadmap of what's next, the relationship with key stakeholders, and the confidence that someone at Pencil is thinking ahead on their behalf. You'll work in lockstep with your Customer Success Technical Manager counterpart, who owns the day-to-day platform experience, while you own the account's trajectory: expansion, renewal, and the story we tell the client about where the partnership is heading. You're the client's proof that someone is thinking ahead about their account and has their back when it counts.

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

Key responsibilities:

• Own the day-to-day commercial and strategic health of a portfolio of accounts, building trusted relationships with the stakeholders who hold the budget and the renewal decision.

• Build and run the account's cadence — QBRs, roadmap conversations, and renewal timelines — supporting in helping bring a clear narrative on where the partnership is heading and why.

• Partner closely with your CST counterpart so nothing falls in the gap between the platform and the account — support patterns feed your account plan, and your account strategy shapes what CST prioritizes.

• Keep account documentation, trackers, and materials complete, current, and client-ready before anything goes out the door — you are the source of truth for your accounts.

• Proactively identify and pursue expansion and upsell opportunities by understanding client goals, usage patterns, and where Pencil can create more value.

Your background:

• 3-5 years of experience in customer success, account management, or client-facing commercial roles, ideally in SaaS, advertising, or marketing tech.

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

• Track record of owning renewals and growing accounts, with strong client-facing communication and presentation skills.

• Comfortable operating one layer up from the tool — thinking in terms of account strategy, commercial structure, and stakeholder relationships rather than platform mechanics.

• Experience building and maintaining clear, organized account documentation (trackers, QBR decks, account plans) that clients and internal teams can rely on.

• Familiarity with subscription-based business models and a genuine curiosity about how generative AI is changing marketing and creative workflows.

You’ll Thrive Here If You…

• You're commercially minded but always focused on client success — you can hold both at once.

• You take ownership of your accounts end-to-end: you don't wait to be asked, you bring net-new thinking to move things forward.

• You communicate proactively and clearly, giving stakeholders visibility before they have to chase you for it.

• You care about polish — the decks, trackers, and materials you send a client are complete and considered before they land in an inbox.

• You enjoy partnership: you build real working relationships with your CST counterpart and with agency partners like OLIVER, rather than working around them.

KPIs & Success Measures

• Account retention and renewal rate across your portfolio.

• Expansion and upsell revenue generated from existing accounts.

• QBR and account plan quality and cadence — consistently delivered, on time, and grounded in a clear narrative.

• Client satisfaction / NPS across your accounts.

• Documentation and tracker currency — account materials are always complete and up to date.

• Proactive communication — stakeholders have visibility into account status without needing to chase it.

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