Sales Development Representative

Sales Development Representative

SiteCare | Remote | Full-time

Read this part first

In the interest of full disclosure, we’ve tried this role before and it didn’t work. Why? Because we handed them a list and a phone and they had no sense of who we are. They went out and sounded like every other outbound rep out there.

The reason we’re saying this openly is because we would rather you opt-out now than three weeks in. 

What SiteCare actually is

We keep business-critical WordPress sites fast, secure and current so our clients can get on with running their businesses. That is the transactional description. Here is the real one.

For many years, we’ve believed that over-the-top customer service reaches further than any ad ever will, and that if we ever had to choose between a new thing for our clients and a big ad campaign, we would pick the clients every time. 

We are trying to be the most caring and capable team in WordPress. That’s the whole strategy.

What you would do

You are the first human a cold lead hears from. These are people who talked to us at some point and it didn’t come together. Your job is to warm them back up and book a call with Ryan Sullivan, our Chief of Staff. That is the number that matters. Everything else is in service of it.

You will work a list Ryan builds and cleans. Email, phone, LinkedIn. Six touches over three weeks, then you leave them alone for 90 days. You log everything in Pipedrive as it happens. You share your numbers at the end of every day, good days and bad days both, and you and Ryan sit down for 20 minutes each morning to go through the actual conversations. The ones that went sideways are the useful ones.

Over time, if this goes well, you would take on pipeline management and eventually prospecting. There is a real path from this seat into a client-facing role for the right person.

Who we are looking for

Someone who can talk to a VP of marketing like a human being and not like a sales robot. There is a narrow lane between sounding automated and sounding smarmy, and we need someone who lives in it naturally. You either have this or you don’t. It’s not a trait that can be trained.

Someone curious about what we sell. Our best guess at why previous attempts failed is that nobody asked how the pieces fit together. If your first week is spent asking what CoreSpeed actually does and why Core Web Vitals matter to a publisher, you’re already ahead.

Someone who says "my bad" fast. Best teammates on any team are the first ones to raise a hand when they missed the mark.

Someone who hears the difference between service and hospitality. If that question makes you think of a specific time somebody took care of you and you can still remember how it felt, we want to talk to you.

Prior outbound experience helps. A CRM you have actually lived in helps. WordPress knowledge is genuinely optional.

What we will give you

A playbook with real scripts, real objection handling and clear lines on what you should and shouldn’t say. Published pricing you quote word for word. Free tools that give you something to offer besides a meeting request. Guardrails, so you are never guessing whether something is okay.

Daily access to Ryan, who will be in your conversations with you for the first several weeks.

Competitive salary, remote, technology stipend, PTO and a team that will not make you do checkbox activity to prove you exist.

What this job is not

It isn’t a volume job. Thirty personalized emails beats three hundred generic ones and we will not congratulate you for the three hundred.

It isn’t a job where you negotiate, diagnose, promise timelines or invent guarantees. When you don’t know, "great question for Ryan" is a complete answer.

It isn’t a job where you chase someone who asked to be left alone. One request stops every channel forever. We treat that as sacred, not as a rule we technically comply with. 

One more thing

When you fill out your application, tell us about a time somebody in a service business made you feel genuinely taken care of, then tell us what you think they did on purpose.

Also, don’t use AI for this. We’ll be able to tell and it’s an automatic disqualfier. We don’t need a novel. Quality > quantity. 

This opportunity is fully remote. Qualified candidates will have native-level comfort with written and spoken English. Typical working hours are Monday - Friday, 9AM - 5PM US Eastern Time.