Hybrid / London / Sponsorship Unavailable
Happy Tree Cards is changing the way teams celebrate together.
We help organisations send thoughtful digital group cards for birthdays, work anniversaries, leavers, welcomes and other meaningful moments, without the admin headache of paper cards, scattered contributions, or missed delivery dates. Our platform combines beautiful design with modern collaboration tools, delivery tracking, reminders, media uploads, and workplace-ready controls. For organisation customers, we also offer shared credits, centralised billing, custom covers, AI moderation, audit logs, and priority support.
Founded in 2021, we are building a product that sits at the intersection of employee experience, workplace culture, and practical software. We are now looking for a Director of Sales to turn strong product-market resonance into a repeatable, scalable commercial engine.
The role
This is a senior, hands-on leadership role for someone who wants to build, not just manage.
You will own the sales strategy and execution for Happy Tree Cards’ organisation growth, with a particular focus on the buyers most likely to feel our value quickly: People teams, HR leaders, Executive Assistants, Office Managers, internal culture owners, and other workplace operators responsible for celebrations, recognition and team experience.
You will work closely with the founder and product team to sharpen our ICP, improve commercial messaging, build a repeatable pipeline, close high-quality opportunities, and shape how sales should scale.
What you’ll be responsible for
Own and deliver the sales strategy for organisation subscriptions, bulk usage, and larger workplace accounts.
Define and refine our core ICP, priority segments, buyer personas, and sales playbooks.
Build pipeline through a mix of outbound, partnerships, inbound conversion, founder-led opportunities, and product-led signals.
Lead the full sales cycle from discovery through demo, proposal, negotiation, close, and expansion.
Translate our product into clear commercial outcomes for buyers, including easier team celebrations, better participation, less admin, improved governance, and stronger employee experience.
Help position Happy Tree Cards as the modern workplace alternative to paper cards, ad hoc collections, and clunky internal processes.
Improve sales fundamentals: CRM discipline, forecasting, reporting, conversion analysis, and pipeline hygiene.
Feed market insight back into product, pricing, packaging, onboarding, and customer experience.
Build the foundations for future sales hiring, whether that becomes SDR, AE, partnerships, or customer growth support.
Represent the voice of the customer internally and raise the quality of our commercial decision-making.
What success looks like
In your first 6 to 12 months, you will have:
sharpened our target segments and buyer messaging;
created a clearer, more repeatable B2B sales motion;
increased qualified pipeline and close rates for organisation customers;
improved how we sell to HR, People, EA, and workplace operations buyers;
helped shape packaging and commercial offers that match real buyer needs;
created the foundations for a scalable sales function.
About you
You are commercially sharp, operationally strong, and comfortable working close to the detail.
You probably have experience in a SaaS, future-of-work, HR tech, employee experience, internal communications, or workplace services business. You understand how to sell to practical, time-poor buyers who care about usability, reliability, governance, value for money, and stakeholder confidence, not just feature lists.
You know how to build trust with decision-makers such as HR Directors, Heads of People, Executive Assistants, Office Managers, People Ops leads, and culture owners. You can sell a product that is joyful and human, while still making a serious commercial case.
We’d expect you to bring
A strong track record in B2B sales, with meaningful experience in a senior individual contributor or leadership role.
Experience building or scaling a sales function in an early-stage or scaling environment.
Confidence owning both strategy and execution.
Strong discovery, demo, objection-handling, and closing skills.
Experience selling into HR, People, Operations, workplace, or culture-led functions.
Commercial judgement around pricing, packaging, and route-to-market.
A structured approach to pipeline management, forecasting, and CRM discipline.
Strong written and verbal communication skills.
A bias for action, experimentation, and learning.
You’ll stand out if
You have sold a product with a product-led or self-serve element and know how to combine that with assisted sales.
You have experience selling relatively affordable, high-usage SaaS rather than relying only on long enterprise sales cycles.
You understand the emotional and operational side of workplace celebrations, employee recognition, and distributed team culture.
You can spot where a simple product solves a surprisingly expensive internal problem.
You enjoy working in a values-led business that cares about community, simplicity, customer care, technology, and experimentation.
Why join Happy Tree Cards
We are building a category with clear emotional resonance and clear workplace value.
The product is easy to understand, easy to demonstrate, and solves a real problem for modern teams.
There is strong room to shape the commercial function from an early stage.
You will work closely with the founder and have genuine influence over growth strategy.
We care deeply about quality, customer experience, and building thoughtful technology.
Our brand is warm and human, but our product is increasingly workplace-ready, with features that matter to serious organisation buyers.
Our values
We care about:
Community
Simplicity
Love for the customer
Nerdiness in how we solve problems
Experimentation and learning
If that combination sounds like you, we’d like to hear from you.
To apply
Please send your CV and a short note explaining why this role and market are a fit for you.