Sales Development Representative
Offsite
Remote
contract
$18000 - 36000
Posted 5 hours ago
Job Description
We’re Seeking An Early-Career, Insanely Ambitious SDR To Join Our Team.
Please read the job description carefully before applying…
Offsite (www.offsite.com) makes it easy to plan team retreats, offsites, and conferences.
Used by hundreds of top startups, Inc 5000s, nonprofits, and other organizations, Offsite is already a marketplace that has facilitated $30M+ in spend on offsites and a growing user/client base.
We’re VC-backed (raised from Automattic, makers of WordPress, as well as Forum Ventures, Ground Game, and 70+ angel investors), capital efficient, and growing.
We’re looking for someone who will (at minimum) book 15+ qualified sales meetings for our team each month through a mix of:
Please read the job description carefully before applying…
Offsite (www.offsite.com) makes it easy to plan team retreats, offsites, and conferences.
Used by hundreds of top startups, Inc 5000s, nonprofits, and other organizations, Offsite is already a marketplace that has facilitated $30M+ in spend on offsites and a growing user/client base.
We’re VC-backed (raised from Automattic, makers of WordPress, as well as Forum Ventures, Ground Game, and 70+ angel investors), capital efficient, and growing.
We’re looking for someone who will (at minimum) book 15+ qualified sales meetings for our team each month through a mix of:
- social selling on LinkedIn (and other platforms),
- lead list-building and outbound email sequences,
- cold-calling
- and “whatever it takes” to not only meet your quota for “meetings booked”, but force us to increase your targets over time and potentially even hire more SDRs to work under you, that you can train on your methods, so we can scale our outbound sales efforts over time.
The ideal candidate would have at least 1-4 years of experience as a SDR for HR Tech or B2B SaaS, leverage AI but still have “taste” in crafting compelling copy for email sequences, and do “whatever it takes” to land this opportunity at Offsite and crush it.
This is a unique opportunity to:
👉 join a VC-backed startup as a contractor (and possibly full-time, salaried with equity and benefits in the near future)
👉 work wherever you want and however you want (so long as you have exceptional WiFi connection, North American and South American candidates preferred and/or working EST hours is a “must” for this role)
👉 build a network of “people leaders” at high-growth companies includings Chiefs of Staff, Executive Assistants, and People Leaders at high-growth companies who use Offsite
👉 be part of a dynamic, fast-growing startup revolutionizing the way teams connect and collaborate in-person
👉 and so much more!
Role Overview
We’re hiring a Sales Development Representative (SDR) to drive new business engagement and help us hit ambitious growth goals. As a SDR at Offsite, your primary mission is to generate qualified pipeline through proactive prospecting, meaningful outreach, and booking qualified meetings per month with target accounts.
You’ll be the first impression many prospective clients have of Offsite - creative, empathetic, pleasantly persistent, and strategic.
You’ll work closely with our Marketing and Sales teams to refine messaging, improve outreach cadences, and identify high-impact targets that accelerate revenue growth.
What You’ll Do
- Prospect & Outreach — Identify, research, and reach out to potential customers via email, phone, LinkedIn, and multi-channel campaigns using tools like Apollo, LinkedIn Sales Navigator, PostHog (product analytics tool) and similar tools, including lead list-building efforts to support the sales team and company executives.
- Lead Qualification — Engage prospects to understand their needs, challenges, and fit; qualify opportunities based on Offsite.com criteria.
- Meeting Generation — Book at least 15 qualified meetings per month (to start) with target decision-makers for our sales team.
- CRM & Tracking — Maintain accurate and up-to-date prospect records and activity in our CRM (HubSpot).
- Feedback Loop — Collaborate with Sales and Marketing to strengthen messaging, targeting, and campaign performance.
- Performance Metrics — Track outreach results, conversion rates, pipeline impact, and key SDR KPIs.
Who We’re Looking For
We want self-starters who enjoy a challenge, thrive in a fast-paced environment, and are eager to contribute to building something great. Ideal candidates will have:
- Proven communication skills (phone, email, social outreach) with the ability to start meaningful conversations.
- Sales hustle - you’re motivated by goals, excited by metrics, and energized by outbound prospecting.
- Organizational skills - you manage your pipeline, data, and time with precision.
- Team mentality - willing to iterate, receive feedback, and help refine SDR best practices.
- Entrepreneurial Mindset - you will help improve/build our playbook, automations, and GTM Ops
- Attention to detail - to demonstrate this, send us your favorite Spotify playlist along with your resume and a 1-2 minute video introducing yourself.
Nice to Have
- Experience with HubSpot and sales engagement tools like Apollo and LinkedIn Sales Navigator
- Familiarity with the group business travel and hospitality industries
- Prior SDR/BDR experience (1+ years preferred but not required)
- Familiarity with SaaS or B2B solutions
Why You’ll Love Working Here
- Build with us - this isn’t a “plug-and-play” box to check; it’s a chance to help define a high-impact sales motion.
- Growth not stagnation - clear paths to advance into your next role, leadership, or specialized sales functions.
- Data & support - you’ll have training, coaching, and tools to help you succeed.
- Impact culture - your contributions directly influence revenue growth and company success.
Comp and Benefits:
The starting compensation for this role is around $3,000 USD per month (half retainer, half commissions tied to the number of qualified meetings booked each month).
We are initially hiring a contractor, but a full-time role may be available with 3-6 months of proven success at Offsite, to earn healthcare, a monthly Remote Work stipend, an annual Health and Wellness stipend, and unlimited PTO as well as stock options in the company.
The starting compensation for this role is around $3,000 USD per month (half retainer, half commissions tied to the number of qualified meetings booked each month).
We are initially hiring a contractor, but a full-time role may be available with 3-6 months of proven success at Offsite, to earn healthcare, a monthly Remote Work stipend, an annual Health and Wellness stipend, and unlimited PTO as well as stock options in the company.
Required Skills
CRMHubSpotCommunicationOrganizational SkillsAttention to DetailLead Generation
About the Company
Offsite
E-commerce / Marketplace
11 - 50
Offsite saves you time, money, and stress.
We help you choose the perfect venue, plan an agenda that engages your employees, and generate measurable ROI on your Offsites. All in one place.
Increase employee engagement, connection, and alignment at your company with Offsite.
Our mission is to help teams stay connected through intentional, in-person experiences. We not only take care of the logistics around corporate retreat planning, but we become your partner in creating a thriving workplace. In short, we care deeply about you and your people.
We help you choose the perfect venue, plan an agenda that engages your employees, and generate measurable ROI on your Offsites. All in one place.
Increase employee engagement, connection, and alignment at your company with Offsite.
Our mission is to help teams stay connected through intentional, in-person experiences. We not only take care of the logistics around corporate retreat planning, but we become your partner in creating a thriving workplace. In short, we care deeply about you and your people.
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Company
Offsite
E-commerce / Marketplace
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