Pilotship.io · Now Hiring
Sales Development Representative
Be the first impression of an AI-native software company — and learn to run the tools the rest of the industry is still reading about.
- Compensation
- $25–35/hr$78–85k OTE with commission
- Location
- AtlantaHybrid
- Type
- Full TimeHourly + commission
- Reports To
- Phil ThorntonCo-Founder
01 / 05 · Who We Are
We build at the edge of what AI can actually do
Pilotship is an AI-native software development consultancy. We build production-grade applications at the cutting edge of what AI can genuinely deliver — AI agents, AI-native products, and intelligent systems that solve real problems for real businesses. We work with founders and established companies to get products to market faster than has ever been possible.
We are small, we move fast, and we are building something that did not exist two years ago. That means the people here do work that has no playbook yet — and get very good at tools most of the industry is still figuring out.
We value people with an entrepreneurial spirit who lean into hard challenges, enjoy solving difficult problems, and do not shy away from hard conversations. We want to be challenged and supported in equal measure. Sound like your kind of people? Keep reading.
Our Values
What connects everyone here
Every person here has their own role. We are all connected by the same handful of things.
Extra Mile Mentality
Going the extra mile is not doing work for the sake of work, or padding hours to look busy. It is actively identifying the genuinely valuable, high-impact things we can do that nobody asked us to do — and then doing them.
We anticipate instead of just executing. We add value unprompted. We measure the extra mile in real impact, never in hours logged. And we do it because we care about the people we serve, not because anyone is keeping score.
Agency
You have real control over your own thoughts, your own behavior, and your own outcomes. We build an environment where you have the confidence to handle a wide range of situations — and the expectation that you will.
Gratitude
We approach each day grateful for the opportunities we have been given. When we hit problems, we look for solutions before we voice complaints.
Curiosity
We are in the business of the brand new. The people who thrive here are relentlessly curious — about our clients’ businesses, about how the technology actually works, about why something didn’t land and what to try next.
Grit
We don’t shy away from difficult challenges, we lean into hard conversations, and we keep the promises we make to ourselves.
02 / 05 · What You’ll Do
You are the first impression
Pilotship is looking for a Sales Development Representative to join our team. You will be responsible for identifying the businesses that fit our customer profile, making real connections with the people who run them, developing a genuine understanding of their problems, and bringing those opportunities forward.
Before a prospect ever sees what we build, they see how we communicate.
This role reports directly to Phil Thornton, one of our co-founders. You will not be buried three layers down in a sales org — you will be working alongside a founder every day.
Key functions in this role
- Identify high-quality prospects against a specific ideal customer profile, using their websites, public signals, and early conversations.
- Create meaningful connections by phone, email, and direct message — real messages to real people, not blast sequences.
- Become an expert at recognizing who you’re talking to and what is actually keeping them up at night.
- Move qualified prospects forward in the sales process and act as an advocate for what they need.
- Use and help build our AI-powered prospecting and outreach tooling — research agents, enrichment pipelines, and personalization systems that let one person do the work of a team.
- Track and report on the key metrics behind your activity, and use them to get better every week.
- Feed what you learn on the front lines back to the team so our positioning stays sharp.
- Collaborate closely across the whole company — sales, delivery, and marketing.
03 / 05 · Who We’re Looking For
Top qualities & experience
- A self-starter with real agency. Nobody here is going to hover over you. You need to be able to look at an ambiguous goal, decide what to do first, and go do it.
- Hungry, and early in your career. This is a role for someone who wants to build a career fast and is willing to do the work that gets them there. Prior sales, business development, or customer-facing experience is a plus, not a requirement.
- Genuinely curious. About technology, about business, about people. You ask good questions and you actually listen to the answers.
- Strong interpersonal, relationship-building, and listening skills. You can hold a real conversation with a business owner and leave them better off for it.
- Excellent written communication. A large share of this job is writing — and writing something a busy executive actually wants to read is a skill.
- Comfortable with technology and eager to learn AI tools. You do not need to be technical. You do need to be the kind of person who opens a new tool and starts poking at it.
- Grit. The willingness to hear no, learn from it, and pick the phone back up.
- Experience with a CRM (HubSpot, Salesforce, or similar) is a plus.
04 / 05 · How You’ll Be Supported
You will not be handed a list and a quota
You will be given the resources and the training to understand exactly what a great Pilotship client looks like and how to help them. You’ll be shown how to approach these businesses, build trust and rapport, and act as a genuine consultant rather than a salesperson. You’ll get expectations and goals that are specific and achievable, a clear understanding of how to reach them, and real accountability to those numbers.
You will also be handed something genuinely rare: hands-on, daily experience building and running AI systems. You will learn to use AI agents to research accounts, to personalize outreach at a scale that used to require a team, and to automate the parts of this job that used to grind people down. You will be working with the same tools our engineers use to build client products.
Most importantly, you will report directly to a founder who cares about you getting better every single day.
05 / 05 · Why This Job Is Different
The honest pitch
Most SDR jobs teach you to work a sequence. You inherit someone else’s list, send someone else’s email, and hit someone else’s activity number. You learn how to operate a machine somebody built years ago.
This one is different because the machine is being built right now — and you get to help build it.
Every week at Pilotship we are figuring out what AI can do that it could not do the week before. You’ll be sitting inside that — using agents to do research that used to take hours, generating personalized outreach that actually lands, and learning, by doing, how these systems really work.
That experience compounds. In two years, the ability to genuinely wield these tools will be one of the most valuable things a person can have on their resume — and very few people will have learned it the way you will: on real work, with real customers, with real consequences.
If you’re hungry, curious as hell, and you want to build a career at the front edge of where technology is going instead of watching it from the sidelines — this is the job.
How to Apply
Send us your resume
We read every application ourselves. No portal, no black hole.
Prefer email? Write to Founders@pilotship.io.