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askdragonfly

Founding Sales Development Representative

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This isn't a traditional SDR role

If your idea of outbound is hitting a dial quota and burning through a sequence tool, this isn't for you. If you measure yourself by meetings booked without caring what happens to those meetings, this isn't for you.

But if you've built your own outbound stack from scratch, used AI to cut research time by 80%, and thought seriously about why most SDR playbooks break down at an early-stage startup, and you have views on what a modern GTM motion should look like, we should talk.

About Dragonfly

Dragonfly is building the world's first Automated Solutions Architect. We help businesses navigate the complex landscape of modern tools (SaaS, AI, infrastructure) by using an AI-powered platform that understands their unique context and recommends the optimal tech stack.

Our platform is powered by a proprietary knowledge graph of 230K+ products, 4M+ companies, and the relationships between them. We've raised a pre-seed from Tier 1 investors and are already working with 20+ world-renowned brands. We're in delivery mode and now building the GTM machine to match.

This is a rare opportunity to join at the earliest stage and own the commercial foundation of a generational product.

The Role

This is Dragonfly's first fully dedicated GTM hire. You're not joining a team, you're starting one. The first 3 to 6 months are about learning the ICP deeply, building the outbound motion from scratch, and booking high-quality meetings with CTOs and engineering leads at mid-to-large organisations.

You'll work directly with Sean (co-founder) and report into the GTM lead. Qualified meetings get handed to Sean for closing. Your job is to find the right people, get them interested, and make the handoff clean.

What You'll Do

In the first 3 to 6 months, you'll be focused on:

  • Building and owning Dragonfly's outbound motion (sequences, messaging, targeting) from zero

  • Identifying and reaching out to ICP accounts (Senior decision-makers, such as heads of function and C-suite executives, at scale-ups and medium-sized enterprises)

  • Representing Dragonfly at events and roadshows, comfortable with in-person pitching and generating pipeline from physical presence

  • Pre-qualifying leads and running high-level Dragonfly pitches before handoff to Sean

  • Recommending and building the GTM stack, with input on what tools we use (Apollo, Clay, Dripify, or whatever you think is right)

  • Working closely with Yoojin (Founder Associate) on messaging, campaigns, and feedback loops between outbound and content

What We're Looking For

Must-haves:

  • 2 to 3 years in a B2B SDR or BDR role, ideally at an early-stage tech startup

  • Consistent quota attainment: the key signal is whether you hit your number, not how long you've been doing it

  • Founding or early SDR experience: you've built from scratch, not inherited a playbook

  • AI-native GTM approach: you use AI for research, personalisation, and efficiency, but you don't outsource judgment

  • Strong written and verbal communication: you can pitch Dragonfly in 2 minutes to a skeptical CTO

  • London-commutable, comfortable with 3 days in the office and occasional events

Strong positives:

  • Conference and roadshow experience — comfortable generating pipeline from physical presence

  • Experience recommending or building a GTM stack at an early-stage company

  • Familiarity with tools like Apollo, Clay, Dripify, LinkedIn Sales Navigator, and similar

  • References ready immediately: quota attainment should be verifiable

The GTM Tools Angle

We're an AI company. We expect our first GTM hire to be genuinely AI-native — not in the abstract, but in practice. That means using AI to cut research time, build better target lists, personalise messaging at scale, and think critically about which tools are worth the cost. You'll have real input into the GTM stack we build.

Compensation and Benefits

  • Base salary: £40,000

  • OTE: £60,000 (uncapped commission)

  • Share-options plan

  • 30 days annual leave plus 8 bank holidays

  • Private health insurance

  • Direct access to founders

  • High-trust, outcome-focused environment

  • Hybrid: Clerkenwell office, Tue/Wed/Thu

The Process

  1. Async video interview (5 questions, 20 minutes — no CV screen alone)

  2. Shortlist based on Video interview (yes we'll be watching all of them)

  3. Meet someone from the Team — a Dragonfly pitch and Q&A (20 minutes)

  4. Deep-dive interview (60 minutes)

  5. Final conversation with one of our Co-Founder

We are an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.