About this role.
Double is hiring a remote US Sales Development Representative to generate pipeline by identifying bookkeepers and securing product demos. The role centers on outbound prospecting through cold calls, email, and social outreach, supported by a strong understanding of Double’s bookkeeping workflow platform. Success requires concise written and verbal communication, resilience, quota motivation, and comfort initiating cold conversations. The position appears suited to an early-career sales professional, with some prior sales experience preferred and a defined progression path to Senior SDR.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
3/5Pace & Pressure
4/5Autonomy Level
3/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would define the ideal customer profile using factors such as firm size, client mix, technology stack, and growth signals. I would then use reputable data sources and LinkedIn to identify relevant contacts, segment the list by likely pain points, and prioritize accounts with clear indicators that Double can improve their workflow.
I would keep it brief, personalized, and focused on a relevant problem rather than leading with product features. For example, I would reference the challenge of managing client work across spreadsheets and disconnected tools, explain one clear outcome Double supports, and end with a low-friction request for a short conversation.
I treat rejection as normal feedback within a high-volume sales process and focus on controllable inputs such as call quality, follow-up consistency, and testing messaging. I review objections for patterns, ask for coaching, and track activity and conversion metrics so I can improve rather than take individual outcomes personally.
I would acknowledge that spreadsheets can work, then ask a discovery question about the time, visibility, or error-management challenges involved in their current process. If there is a meaningful pain point, I would connect it to Double’s value and propose a demo; if not, I would leave the conversation positively and schedule an appropriate follow-up.
I would use a structured cadence across calls, email, and social channels while tailoring the opening message to each prospect segment. I would monitor conversion rates by channel and persona, double down on approaches producing qualified meetings, and maintain accurate CRM notes so follow-ups are timely and contextual.
About Double
Bookkeepers today are stuck working in excel spreadsheets and homegrown project management solutions to support their clients. Double is on a mission to change that.
With our all-in-one tool, bookkeepers can manage their work, communicate with clients, catch hard-to-find errors, and deliver reports to help their small business customers make smarter strategic decisions.
Founded in 2021, Double has raised $12M in funding, backed by leading tech investors like Y Combinator and founders at top startups like Lattice, Front, Superhuman, Plaid, and more. Double currently helps thousands of bookkeepers and accountants manage the books for startups and small businesses across the US.
What You’ll Do
Your job is to find bookkeepers and convince them to schedule a demo with us.
Here’s what that looks like on a day-to-day basis:
Find prospects and engage them through calls, emails, and social media
Develop a keen understanding of Double’s product and why people buy it
Write clever emails that make people smile and reply
Who You Are
You write and speak clearly and concisely
You are excited to get after it and crush quota
You are willing to eat the frog and make cold calls
Some sales experience preferred
Benefits
Competitive pay and equity
Unlimited PTO
Health, dental, and vision insurance
Automatic promotion path to Tier 5 Senior SDR
Double provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.
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