About this role.
WorkWhile is seeking a Sales Development Representative to generate new business by identifying prospects, conducting outbound calls and emails, and booking qualified appointments. The role involves managing contact lists, researching ideal customer profiles, organizing outreach by geography, and maintaining detailed CRM notes. This early-stage sales position emphasizes experimentation, ownership, and building repeatable SDR processes within a fast-growing startup. The successful candidate will be goal-oriented, organized, resilient, and comfortable working in an evolving, high-velocity environment.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
3/5Pace & Pressure
5/5Autonomy Level
4/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Sales Development Representative role at WorkWhile. I bring a goal-oriented, organized approach to prospect research, multi-channel outreach, and qualifying conversations that create clear next steps for sales teams. WorkWhile’s mission to improve stability and opportunity for hourly workers strongly resonates with me, and I would welcome the chance to help build repeatable outbound processes in a fast-moving environment. I am eager to contribute my persistence, curiosity, and ownership mindset to help expand WorkWhile’s client base.
Sincerely,
Applicant
Sample interview questions
I segment prospects by ideal customer profile fit, geography, company signals, and likely urgency. I then prioritize high-fit accounts, use a consistent outreach cadence, and review response and meeting-conversion data to refine the list weekly.
I would confirm the prospect’s role, current workforce or staffing challenges, urgency, relevant business impact, and openness to exploring a solution. I would document these details, the agreed next step, and any objections in the CRM so the account executive can run a relevant discovery meeting.
I treat rejection as useful feedback rather than a personal setback. I maintain activity discipline, test messaging and channels, review objections for patterns, and focus on controllable inputs such as preparation, personalization, and timely follow-up.
I would track outreach volume, contact rates, reply rates, positive response rates, meetings booked, meeting-show rates, conversion to qualified opportunities, and CRM data quality. Reviewing these metrics by segment and messaging helps identify where adjustments will have the greatest impact.
I would document effective messaging, qualification criteria, objections, cadence steps, and prospecting workflows as I learn. I would share results with the sales team, run small tests, and turn successful practices into simple playbooks that can be measured and improved.
About WorkWhile
WorkWhile is on a mission to help workers earn a better living and live better lives. 83 million Americans work hourly jobs, often with unpredictable schedules that pay close to minimum wage and offer limited benefits, leading to financial instability.
WorkWhile identifies the best hourly workers and matches them with shifts that fit their skills, location, and life. Businesses get access to a quality workforce, while workers get stable income and unmatched benefits, including next day pay, free telehealth services, and financial services.
We have the audacious goal to align incentives and solve inefficiencies in the labor market, disrupting the $650 billion staffing and recruiting market. Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, WorkWhile is reshaping the future of work.
About the role
WorkWhile is looking for an exceptional Sales Development Representative to reach out to potential new clients and set qualified appointments with clear next steps. As an early member of the team you will help create repeatable actions in the daily SDR process that lead to success and shape all aspects of SDR culture. You will be responsible for all sales outreach and will partner closely with our sales team to drive success in acquiring new business for WorkWhile.
Manage a list of contacts from different company profiles and reach out to these contacts in a timely manner
Identify and understand WorkWhile’s ideal potential client and reach out to similar companies
Create outreach to companies and contacts in an organized manner by geo location
Use outreach tools and job boards to identify new leads and reach out to them via call and email
Set qualified appointments by setting the right expectation and finding pain points
Exceed monthly appointment setting goals. Place detailed email and call notes in our CRM for the sales team to make sure that next steps are clear
About you
Goal and solutions-oriented professional who is creative, ambitious.
Self – motivated who is hungry and scrappy in finding a way to hit monthly goals.
Detailed and Organized when setting up priorities for the week and month.
Able to pick things up quickly and work in a fast-paced ever-changing environment.
Someone who is open to new ideas and able to implement and test those ideas.
Someone who has experience working within a fast-paced Series A or Series B Start-up
Benefits & Perks
Hybrid work culture with office hubs in SF, NY & Toronto
In-person company offsites
Medical, dental, & vision coverage
Flexible time off
401(k) with employer match
WFH stipend to support your home office needs
WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply. WorkWhile has a diverse, mission-driven, and supportive culture—we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!
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