Hi, I'm Joe, Head of Customer Success at Whippy. I'm hiring an entrepreneurial CSM to retain and grow a dedicated book of customers.

WHY I'M HIRING

At Whippy, we value our CSMs even more than our sales reps because if customers don't get value from a tool, they'll leave. Whippy has six incredible products today because we've always built alongside our customers - that's how we evolved from a simple texting platform to now powering calls, texts, email, Ai-agents, and complex messaging and business automations for over 1000+ businesses. We ship fast to meet our customers' needs.

Most customers start with one use case, like a staffing firm using an AI voice agent to screen candidates. They stay and grow because they see real ROI, then expand use cases until Whippy becomes the infrastructure their business runs on. Your job is to drive that growth: make their first outcome happen during onboarding/implementation, uncover the next problem, and help them get even more value.

Our best CSMs have taken our staffing customers from an initial $12k deal to $180k ARR because customers like Your Employment Solutions https://www.linkedin.com/feed/# are getting over $1M in ROI using Whippy to augment their teams and beat the competition.

You'll help us grow more customers by deeply understanding their desired outcomes, helping them achieve those outcomes, and providing an exceptional experience along the way.

This is one of those rare jobs with massive growth and learning opportunities: there's no bureaucracy here, and we're still early in building a world-class customer success team. You'll have a crucial role to play, and fresh ideas, feedback, and experimentation are always encouraged because we double down on wins and quickly pivot when ideas don't work out.

You'll work with six other CSMs and report directly to me, and I'll provide the support, coaching, tools, and data to do the best work of your career here, plus the variable comp to get well rewarded when you deliver results.

I'm looking for a CSM that wants to grow into a renaissance CSM, someone technical, strategic, and commercial, all in one: Technical as in you enjoy mastering the product and finding the best solutions for our customers. Strategic as in you deeply understand your customers pain points and always have a plan to solve them. Commercial as in you have pricing awareness and understand the retention and expansion risks and opportunities in your book.

SOME THINGS YOU'LL DO

• Own a book of business end to end, from onboarding through renewal and expansion, as the single point of contact and trusted advisor.

• Own your gross and net revenue retention, and get rewarded for beating targets.

• Run a proactive cadence on every account: prepared calls, clear agendas, mutual success plans, and follow-through.

• Become a product and customer expert. Master Whippy’s products and know your customers' business well enough to build the workflows, AI agents, and automations that solve their problems.

• Tie usage to business outcomes, and report value back in the metrics customers actually care about.

• Turn wins into case studies, references, and testimonials that help sales win the next customer.

• Spot expansion signals and hand warm leads to sales when usage outgrows the contract.

• Tell customers the truth, steering them away from work that won't move their business and toward the work that will.

• Advocate for the customer. Feed what you hear to product, sales, and engineering so we build the right things.

• Experiment and iterate. If you have an idea to do something better, do it and document what you learn.

OUR CUSTOMER SUCCESS VALUES

This is a high-performance environment, and I'll coach & support you through it. You'll be challenged, coached, and you'll always know where you stand. CS is a team sport, so it's okay to ask for help, experiment, fail, and pivot. A few things that are true here:

• Everyone is a builder. Our CSMs build in the product without engineering, and the best product ideas come from you, the person closest to the customer. We use AI to move fast, but we own our work, verify every fact, and don't ship slop.

• We lead with expertise, not order-taking. We get curious about the why behind every request, and we say no when no is the right answer.

• We work like owners, not clock-watchers. We care about outcomes, not hours. We take initiative, pick up the phone, and work obsessively on the problem in front of us.

• CS is a revenue engine, not a cost center. We treat it as the growth engine of the company and pay for results.

WHAT WE'RE LOOKING FOR

• Communication above all. This is the number one predictor of success in this role. You overcommunicate by default with customers, your team, and me. You're clear in writing and on calls, you set expectations, and you never leave people guessing.

• Curious, coachable, and low-ego. You're a fast learner who wants feedback, digs into the why behind every request, and gets better quickly.

• Comfortable getting technical. You don't need to code, but you're the kind of person who enjoys taking a tool apart, figuring out how it works, and building something useful with it.

• Strategic and commercial. You see usage and growth, not just tickets, and you're comfortable owning a number and an upgrade conversation.

• Opinionated about customer experience. Good strategic advice needs well-formed views, so have them.

• Self-directed. You take initiative, stay organized without being told, and run your own book without anyone managing your calendar. Calm under pressure.

• Ideally 2+ years in a customer-facing role (CSM, account management) at a technical SaaS product. That's the preferred path, but if you have an unconventional work history and can articulate how that'll help you succeed in this role, I welcome you to apply

• Fluent written and spoken English required. Able to work US Eastern hours (work starts at 8am)

YOU'LL THRIVE HERE IF...

• You're technical and love to build.

• You're entrepreneurial. You treat your accounts like your own business and get energy from building from scratch.

• You're a consultative problem solver. You dig into the why behind what a customer asks and recommend the right solution, even when it's not the one they came in asking for.

• This sounds like fun to you: a customer wants to launch a complex, time-sensitive campaign across calls and texts, isn't sure how to structure it, and their team is stretched thin. You roll up your sleeves, map their goal to the product, and build it with them.

• You thrive in a fast, evolving startup and you're excited to help build a customer success program from the ground up.

ABOUT WHIPPY

Whippy is a communication, automation, and AI agent platform. You reach customers across calls, texts, and email, at scale through personalized blasts and automated drips, with every message landing in one shared inbox. Replies get auto-assigned to a teammate, picked up by an AI agent, or carried forward by an automation. Once a conversation wraps, Whippy pushes the data you care about back into your systems in the exact format you need. It's true two-way dialogue on every channel that cuts the repetitive work and frees teams to focus on the human work that drives revenue, without adding headcount.

We're industry agnostic, with our biggest wins so far in staffing, healthcare, and other in-person businesses going through digital transformations. We're bootstrapped, profitable, and growing fast, with over 1,000 businesses using Whippy worldwide. In staffing alone, we've helped firms cut screening costs by 95% and save over a million dollars a year.

Whippy was founded in 2021 by CEO David Daneshgar and CTO Jack Kennedy. Jack is an engineering machine and a marathon runner. David started BloomNation in 2011 after winning $27,205 in a poker tournament, grew it into a platform generating billions in sales for florists, then left to build something bigger with Jack.

Location

Candidates based in Buenos Aires, Argentina are strongly preferred as we have a WeWork office in Vicente Lopez and are building toward an in-person team culture. Open to strong candidates anywhere in Latin America or U.S. EST hours required. Full English fluency required.

Compensation

Competitive compensation based on experience, including monthly performance bonuses, WeWork membership, and more.

Hiring Process

1. You submit your application and I'll review it.

2. A 45 minute call with me for us to get to know each other better.

3. You’ll receive a take-home assignment that will assess your technical and strategic skills. The assignment will be presented to me in an hour call. This is your chance to showcase your skills.

4. A 30 minute call with our CEO, David

5. A 30 minute call with our CTO, Jack