Chicago Sales Development Representative
BrightEdge · Sales & marketing tech
On-site in Chicago, IL
SDR/BDREntry-level friendly$72k–$95k baseGrowth stageTraining program
Still open · always hiring (they keep this posting up and hire in groups)
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Sales Development Representative
Simple AI · Sales & marketing tech
On-site in San Francisco; must live near San Francisco, CA
SDR / BDREntry-level friendly$120k OTE
Opens the job on Simple AI's own careers site. Some companies ask you to create an account or click through another page first.
At a glance
What you'd actually do: Research accounts, cold call and send outbound messages to book meetings for the sales team selling voice AI agents.
Pay
$120k OTE
$120k OTE plus equity
Where you work
On-site in San Francisco; must live near San Francisco, CA
Selling to
enterprise customer operations teams
How you'd sell
Mostly outbound (cold calls, emails)
Experience asked
None
Tools you'll use
HubSpot, Salesforce, Apollo, Outreach
Visa
No visa sponsorship
Your game plan for this job
0 of 5 doneMost people just hit Apply. Do these first and you show up with someone on the inside.
- 1Pick 2–3 people at Simple AIWe found 3 current reps: 1 SDRs, 2 AEs. SDRs reply the most; they were in your shoes recently. See them ↓
- 2Send a short, curious noteAsk about their experience, not for a referral. We write it for you, with the role and what Simple AI sells.
- 3Have a 15-minute chatGood questions for this role:
- What does a normal day look like for you?
- How did you land the job? What stood out in your interviews?
- The role is mostly outbound. How much is calling vs. email vs. LinkedIn?
- The posting mentions HubSpot, Salesforce, Apollo, Outreach. How much of your day is in those tools?
- 4Apply, ideally with a referralIf the chat went well, ask if they'd refer you or point you to the hiring manager. Then apply and let them know so they can flag it.
- 5Prep for the role playSDR interviews almost always end in a mock cold call. Practice with the Simple AI cheat sheet and the role-play guide.
Talk to someone at Simple AI before you apply
A friendly message to a current rep is the best way to stand out. Ask about their experience, not for a referral.
Full job description
About Simple
Simple AI is building state-of-the-art voice AI agents for enterprise. Our realistic agents help iconic businesses like Doordash, xAI, and Omaha Steaks handle all kinds of phone operations, from customer support to order intake to lead qualification. We’re growing revenue like crazy and looking to hire a
Sales Development Representative (SDR)
to help accelerate outbound growth and open new markets. We are very excited about the potential for AI to change the world, and work out of our SF office.
Simple AI raised $14M from world-class investors and operators like Y Combinator, First Harmonic, Massive Tech Ventures, Michael Seibel, Jared Friedman, Alexandr Wang, Matt Van Horn, Suhail Doshi, and Scott Wu.
The Team
The founders (Catheryn and Zach) met while running software teams at YC, where they shipped tons of new products for YC founders, including YC’s co-founder matching site. Cat previously worked at Instagram and Facebook and earned degrees in math and computer science at MIT. Zach previously studied computer science and statistics at U Chicago and led software at PEAK6. We have grown into a strong team of 20+ and are continuing to scale quickly.
About the Role
We are looking for an SDR with 0–3 years of experience in an SDR or BDR role to help build the top of our sales funnel from the ground up. You will be responsible for researching target accounts, writing outbound messages, cold calling prospects, qualifying interest, and booking meetings for the sales team.
This is a hands-on, high-activity role for an experienced outbound seller. You will work closely with the GTM team to test messaging, learn which buyers respond, understand different verticals, and help create the early outbound playbook for Simple.
The best fit for this role is someone who is energetic, competitive, resilient, and excited to spend a lot of time on the phone. You should be comfortable with rejection, eager to improve quickly, and motivated by owning outbound pipeline and improving results at a fast-growing AI startup.
What We Offer
Competitive salary & meaningful equity
Employee-friendly equity terms
An office located in SF
Health, dental & vision insurance
Free lunch & dinner at the office
Late night Ubers
Regular team events & offsites
What You'll Need
0–3 years of experience in an SDR or BDR role, with hands-on outbound prospecting and cold calling.
Strong written and verbal communication skills.
A high level of energy, resilience, and comfort with rejection.
Ability to stay organized and thrive in a fast-paced, ambiguous environment.
Curiosity and genuine enthusiasm about AI and how businesses use it.