Join Our Team as a Creative Sales Development Representative (North America)

Location: Remote | People-Centric | Full-Time | B2B Marketplace

Company: Connect with us on Instagram: retreatsandvenues

Be a part of a company that champions the idea that exceptional talent can flourish from anywhere.

If you have a knack for initiating conversations and crafting memorable experiences, you’re the perfect fit for our team. Help us link culture-driven organizations with remarkable retreats that inspire and delight.

About Us

At RetreatsAndVenues, our mission is to help People Leaders effortlessly plan impactful company retreats, ensuring teams depart feeling aligned, connected, and engaged.

Our innovative platform simplifies the process of sourcing, comparing, and booking retreat venues worldwide, saving time and costs while fostering unforgettable connections among remote teams. We’re highly regarded by HR professionals, operations leaders, and advocates for company culture within some of the most innovative organizations today.

As we expand rapidly, we’re seeking a creative, inquisitive, and video-savvy Intermediate-Senior Sales Development Representative (SDR) to elevate our efforts to the next level.

Key Responsibilities

This role goes beyond the typical SDR position.

You will embody a blend of copywriting, education, and connection to spark engaging conversations with B2B People Leaders. Expect to create compelling emails, produce quick videos, facilitate webinars, showcase product demos, and maintain a dynamic CRM enriched with valuable insights. This is a multifaceted, persistent role where effective outreach sets you up for success. Our bonus structure offers uncapped potential for those who deliver high-quality work!

Your contributions will play a vital role in how teams globally build connections, cultivate culture, and thrive together.

What We Offer:

• Completely remote work – enjoy the freedom to work from anywhere, indefinitely.
• Flexible hours – your results take precedence over the clock.
• Competitive pay – earn between $40K and $68K USD in on-target earnings.
• Monthly uncapped bonuses – your success is rewarded continuously.
• Defined career progression – real opportunities for growth based on performance.
• Diverse global culture – be part of a fun team that values autonomy.
• Three weeks of paid vacation annually – plus a break from December 24 to January 1.
• Eleven paid statutory holidays – with options to switch up to three per year.

Your Daily Activities Will Include:

• Crafting persuasive outbound emails that lead to opens, responses, and meaningful dialogues.
• Analyzing response metrics to enhance campaign effectiveness through insights and instincts.
• Engaging with prospects through personal replies to inbound and outbound emails, steering them towards discovery calls.
• Maintaining and expanding our repository of email templates while ensuring CRM data is precise and actionable.
• Enriching prospect profiles by gathering insights from initial contact through to discovery.
• Managing the top of our sales funnel – from identifying targets to engaging and qualifying prospects.
• Overseeing inbound inquiries via our chat platform, using established playbooks to qualify and convert visitors into leads and scheduled calls.
• Creating personalized Loom videos for engaged leads.
• Employing Amplemarket and social media tools to conduct strategic research and form connections with new accounts.
• Transforming Marketing Qualified Leads (MQLs) into Sales Qualified Leads (SQLs), and ultimately into Qualified Booking Opportunities (QBOs).
• Leading or co-hosting succinct, educational webinars aimed at HR and People audiences.
• Being video-ready for discovery calls and creating personalized content for prospects.
• Delivering clear and engaging product demonstrations that address the distinct needs of People leaders.
• Refining and testing email sequences for leads originating from inbound channels.
• Utilizing platforms like LinkedIn, video, and chat for authentic, creative outreach.
• Following up with determination and kindness – being proactive without being pushy.
• Collaborating with marketing and customer success Teams to share insights on effective strategies.

Tools & Technologies You’ll Utilize (Familiarity Preferred)

• Apollo.io – for sequencing, enrichment, and prospect engagement management.
• Amplemarket – for advanced prospecting, email optimization, and multi-channel outreach.
• Close – to manage our CRM and oversee pipeline communications.
• Instantly – for effective inbox management and warm-up strategies.
• G-Suite – particularly Gmail, Sheets, and Calendar for daily operations.
• LinkedIn Sales Navigator – for targeted outreach and account intelligence (familiarity with HeyReach is a plus).
• Loom – for creating personalized pitches and demonstrations.
• Slack – for internal communication and project updates.
• Webinar platforms (e.g., Zoom, Google Meet, or Butter) for hosting live sessions.
• CRM best practices – adept at organizing and enriching data.
• Basic analytics skills – capable of interpreting and acting on open, click, and reply rates.
• Notion or similar tools – for documenting outreach strategies, playbooks, and key learnings.

You Might Be the Ideal Fit If:

• You thrive on initiating conversations and forging connections.
• You are comfortable and confident on video – recording, presenting, and demonstrating effortlessly.
• Your writing skills shine through in concise, engaging emails that feel personal.
• You enjoy experimenting with various outreach tactics and tools.
• You’re organized and curious, eager to understand your target audience deeply.
• You bring experience in B2B sales or marketing (bonus if focused on HR/People teams).
• You flourish in a startup or early-stage environment that moves quickly.
• You have a polished LinkedIn profile and are active on the platform.
• You see the transformative potential of retreats to strengthen teams and enhance collaboration.

Compensation Structure:

1. On-Target Earnings (OTE): $40,000 – $68,000 USD for candidates in the USA, converted to CAD for those in Canada.
2. Compensation Breakdown: 60% Base Salary / 40% Commission.

Ready to make an impact?

Submit your application today by clicking the provided link, completing the survey questions, and recording a short video response at the end. Incomplete submissions will not be reviewed. We will contact shortlisted candidates soon!