Sales Development Representative

About Wholesail (www.paywholesail.com)

Wholesail empowers 400+ wholesalers to confidently manage payment risk without compromising customer relationships or growth. By combining credit onboarding tools, automated AR communications, a payment portal, and accounts receivable workflow tools, Wholesail helps customers get paid 35% faster, streamline AR processes, reduce credit card costs, and enhance the customer experience.

Wholesail was founded by serial entrepreneurs to facilitate enduring relationships between food and beverage wholesalers and their restaurant and grocery buyers. The company is well-funded, with backing from a half dozen venture capital firms and more than 20 angel investors with backgrounds in fintech, payments, SMB marketplaces, and distribution, including early team members from Stripe, Square, Dropbox, Yelp, OpenTable, and Everlane.

About the Role

As a Sales Development Representative, you’ll be the first point of contact for finance and operations leaders at SMB, mid-market, enterprise organizations. Your role is to identify new business opportunities, connect with prospective customers, and articulate how Wholesail can solve real pain points in accounts receivable, payment operations, and credit management.

You’ll use a thoughtful, research-driven approach to outbound prospecting and learn to tailor messaging to different buyer types. This is a foundational sales role designed to help you develop the skills needed to succeed in strategic, high-impact selling. You’ll work closely with Account Executives and sales leadership to create a pipeline and move accounts through the early stages of the sales process.

Responsibilities

• Use modern sales tools to identify businesses within Wholesail’s ideal customer profile across a variety of business sizes and markets.
• Engage with prospects at scale via cold calling, emailing, and social selling (e.g., LinkedIn).
• Reach out to businesses in your pipeline at scale through cold calling, emailing and social selling.
• Promote urgency through a solutions-based sales approach, identifying challenges with businesses and providing targeted value around how Wholesail can help.
• Partner directly with Account Executives to identify winning strategies for outbound prospecting.
• Develop a deep understanding of Wholesail’s value proposition and products to effectively communicate their benefits to prospects.
• Adapt and think on your feet. Whether it’s refining your approach to a tough prospect or finding creative solutions to get in front of decision makers, your problem-solving skills will be key.
• Grow your career in sales through frequent developmental opportunities and mentorship from the Account Executive team.
• Consistently attain and exceed your monthly quotas.

Requirements

• Strong interest in building a career in SaaS sales.
• Clear and confident communication skills, both verbal and written.
• Interest in business operations, finance, or the food and beverage industry.
• Comfortable making cold calls and writing prospecting emails.
• Organized and detail-oriented, with the ability to manage a high-volume outreach pipeline.
• Self-motivated and eager to learn in a fast-paced environment.
• Team player who values feedback and coaching.
• Experience with or willingness to learn modern sales and automation tools (e.g., Salesforce, SalesLoft, Gong, ZoomInfo and AI-powered prospecting platforms).
• A BA/BS degree or equivalent practical experience.
• Prior SDR or outbound sales experience is a plus.

Benefits

• Work with experienced tech startup founders and a customer centric team.
• Compensation based on experience: $50K-$70K base + $20K-$30K bonus opportunity.
• Medical, dental, vision, short-term disability insurance, and 401K.
• $100 per month phone stipend.
• $50 reimbursable monthly expense for work-from-home internet.
• 15 PTO (Paid Time Off) and 5 paid sick days per year, including paid holidays.

Employment Type

• [Employment Type not specified]

Location Type

• [Location Type not specified]

Salary

• $50K-$70K base + $20K-$30K bonus opportunity