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How to Actually Get Hired
Who reads applications, which channel gets a reply, and what they screen for.
Why applying the normal way doesn't work
With only <50 employees, Caddy doesn't have dedicated recruiters. Founders review applications between running the company. The challenge isn't competition — it's visibility. Direct outreach wins.
Who to contact at Caddy
We're still mapping Caddy's hiring process. At this size (<50 people, B2B, Engineering, Product and Design), a founder or department head typically decides, but we haven't confirmed it yet.
What Caddy screens for
B2B, Engineering, Product and Design companies at typically screen for relevant experience and ability to operate autonomously — proof of work beats pedigree.
Tailor your CV to the specific Caddy role rather than sending a general one. Applications that mirror the language of the job description clear automated filters at a materially higher rate.
Mistakes that kill applications
Don't send the same CV you sent everywhere else. At <50 people it's obvious, and it's the fastest rejection there is.
Nobody cares what you want. Start with is growing fast after their null round and how you'd help.
Most B2B, Engineering, Product and Design applications get ghosted. A day-five follow-up can double your response rate.
Frequently asked questions
How do I apply to Caddy?
Through the roles on our Caddy jobs page, or directly to a founder or department head if you can reach them. At <50 people, direct outreach outperforms the form.
Does Caddy respond to cold emails?
We haven't verified response rates at Caddy yet.
Who is the hiring manager at Caddy?
At this size, hiring is usually run by a founder or department head.
How competitive is it to get hired at Caddy?
Roles at <50-person B2B, Engineering, Product and Design companies typically draw 50-100 applicants in the first two weeks. Applying inside 72 hours of a posting going live is the single biggest lever you control.
Have your application sent for you
Get in early at companies like Caddy. We find roles fast, tailor your CV, and apply while the pool is small.
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