Sales Development Representative

About Letterhead

With Letterhead, your newsletters do all the work for you. We help publishers and marketers engage their audience, create great content products, and generate revenue, with software that automates the entire process through machine learning.

We're a venture-backed startup on a journey to change how online engagement happens through meaningful, first-party content. Our founders came from the media industry, building a national network of local email newsletters, and spun out Letterhead in 2022 to help every organization master email.

Our team
We're a diverse team of internally-motivated, open-minded people who want to be the best at what we do. We value intellectual curiosity, candor, and a sense of urgency. When we hire, we look for cultural contribution rather than culture fit: what will each new person add to our team as we grow?

Our company values:
  • Users first: we're here to help our customers, and we put their experience and priorities first.
  • Integrity: we're honest and transparent with each other and our stakeholders. We do what's right.
  • Servant leadership: our best work happens at the front line. Our leadership team exists to support and drive that forward. 
  • Grit: Building something new is hard work. We stick with it, push through obstacles, and get the job done.

Job Description:

As a Sales Development Representative at Letterhead, your primary responsibility is to identify and qualify new sales opportunities, acting as the first point of contact for potential clients. You will be responsible for conducting outreach through various channels, such as email, phone calls, and social media, to generate interest in our software solutions. Your excellent communication skills and ability to build relationships will be essential in helping to grow our customer base and drive revenue for the organization.


Conduct outbound prospecting activities, including cold calls, emails, and social media outreach, to identify and engage potential clients

Qualify leads by assessing their needs, budget, and decision-making process, ensuring they are a good fit for our solutions

Schedule product demos and meetings between potential clients and our Account Executives, effectively handing off qualified leads for further nurturing and closing

Maintain accurate records of all activities, leads, and opportunities in our CRM system, specifically HubSpot

Collaborate with the marketing and sales teams to develop targeted outreach campaigns and refine messaging strategies

Meet or exceed monthly and quarterly targets for qualified leads and opportunities generated

Continuously update your knowledge of our product offerings, industry trends, and competitive landscape to better position Letterhead's value proposition


Bachelor's degree or equivalent experience in Business, Marketing, or a related field

1+ years of experience in sales, business development, or a similar role, preferably within the SaaS industry

Strong communication and interpersonal skills, with the ability to build rapport and engage with potential clients

Experience with various prospecting channels, including cold calling, emailing, and social media outreach

Proficiency in CRM systems, specifically HubSpot

Knowledge of is not required but would be a plus

Self-motivated, with the ability to work independently and as part of a team

Excellent organizational and time management skills, with the ability to multitask and prioritize effectively

What We Offer:

Competitive salary and performance-based incentives ($50k base, $80k OTE, based on experience)

Best-in-class health, vision, and detail insurance with full family premiums on all plans paid 100% by Letterhead

401(k) plan

15 days of paid time off (PTO) per year

Remote work environment with a supportive and collaborative team

Opportunities for professional growth and advancement within the company

Keywords: Business Development Representative, Lead Development Representative, Lead Qualification Representative, Prospecting Representative, Sales Prospector, Sales Lead Generator, Sales Development Associate, Account Development Representative, Inside Sales Representative, Outbound Sales Representative, Telesales Representative, Cold Calling Representative.


Remote (miami, Florida, US)

Remote (Canada)

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