Senior Account Executive in Winnipeg

DTC is a fast-growing B2B media outlet reaching over 155,000 ecommerce marketers and brand founders. Since 2020, we’ve delivered actionable insights that inform, inspire, and entertain operators navigating the fast-changing digital marketing landscape. As our audience, products, and partnerships continue to expand, we’re seeking a Senior Account Executive to join our Partnerships team. This is a high-impact, full-cycle sales role for an experienced seller who can independently drive new business, manage relationships, and grow long-term revenue partnerships across DTC’s ecosystem of newsletter, podcast, and social platforms.

You’ll work directly with the Director of Sales and collaborate closely with our Content and Client Success teams to shape campaigns that deliver real results for industry-leading SaaS, Martech, and ecommerce brands.

REQUIREMENTS:

• 5+ years of full-cycle B2B or media sales experience with a proven track record of prospecting, securing new business, and consistently exceeding sales goals.
• Strong understanding of digital media, ecommerce, SaaS, and B2B marketing.
• Expertise in managing the full sales cycle — from outreach prospecting to renewal.
• Consultative selling skills with ability to build multi-channel campaigns and custom proposals.
• Proficiency with CRM tools (HubSpot preferred) and prospecting platforms (Apollo, LinkedIn Sales Navigator).
• Excellent written and verbal communication; confident presenting to C-Suite executives.
• Self-motivated, strategic thinker comfortable in a fast-paced, startup-style environment.

ESSENTIAL QUALITIES:

• Entrepreneurial: Thrives on autonomy, accountability, and building relationships from the ground up.
• Strategic Thinker: Sees the bigger picture to creatively align client goals with tailored DTC solutions.
• Collaborative: Works seamlessly with both external and internal teams to deliver exceptional client outcomes.
• Data-Driven: Uses performance insights to drive renewals and upsells.
• Resilient: Combats rejection with professionalism and learns from every interaction.
• Leadership-Minded: Sets the tone for the sales team through performance, process, and professionalism.

THE DAY-TO-DAY:

• Pipeline Growth & Business Development: Own outbound strategy: research, prospect, and reach out to new partners across current client areas (SaaS/Martech) and break into other relevant verticals. Build and maintain a robust pipeline aligned to personal revenue goals. Drive new business through creative, consultative selling — not transactional pitches.
• Strategic Sales Execution: Lead discovery and consultation calls, uncovering client objectives and pain points. Develop and present multi-channel campaign recommendations (newsletter, podcast, social, and other integrated products). Manage pricing, contracting, and negotiation to deliver long-term client value. Forecast revenue accurately and contribute to quarterly planning with leadership.
• Account Growth & Retention: Serve as the primary relationship owner for assigned accounts. Partner with Client Success to ensure seamless campaign delivery and measurable results. Drive renewals, upsells, and cross-channel expansion through proactive engagement. Use data and feedback loops to strengthen client partnerships. Share learnings, feedback, and best practices to improve team performance and sales playbooks. Support onboarding and mentorship of junior AEs as the team scales. Collaborate with the Director of Sales to identify new product opportunities and category growth areas.

ABOUT THE POSITION: As a Senior Account Executive, you’ll play a pivotal role in shaping DTC’s next phase of revenue growth. This is a full-cycle, high-autonomy role designed for a confident closer who can balance generating their own leads and account growth. You’ll have access to strong internal support (client success, marketing, and content teams) while being trusted to manage your own book of business and hit meaningful revenue goals.

WHO WE ARE: Since 2020 the DTC Newsletter & Podcast has been sharing actionable advice on how ecom operators and marketers can grow their business and improve their marketing skill set. Our content helps them navigate the ever-changing waters of digital marketing, including creative trends, traffic platforms, technology, and industry news/commentary. Every week we send out 5 newsletter issues, publish multiple podcast episodes and provide topical news coverage through our socials. Our advertising partners thrive within the DTC ecosystem, benefiting from our years of experience, educational content, and highly qualified audience—delivering real results.

APPLICATION INSTRUCTIONS: Along with your resume, please submit a cover letter and a brief explanation of why you are interested in this position. Feel free to include an example of some of the awesome things you've done, both professional and personal achievements that make you stand out. We appreciate your time and thank all applicants for their interest, but we will only be responding to shortlisted applicants.

BENEFITS: Perks for our online team members: Benefits package through Sun Life after completion of the 3 month probationary period. Fun virtual events - we host company events to focus on fun and growth. Work from home. Perks for if you’re ever in town: Commuter friendly - we have bike storage inside our office. Beer on tap - cold, local beer waiting for you.

COMPENSATION: $120K-$150K+ OTE (on target earnings, comprised of base salary + commission).