Account Executive - Small & Medium Size Businesses

Job Title: Account Executive – Small & Medium Size Businesses (AE, SMB)

Company Description:

CYPHER Learning is leading the necessary disruption of learning platforms to unleash human potential with modern learning experiences. We exist to ignite lifelong learning passions through personalized, engaging, and limitless learning experiences for all, giving L&D pros and educators more time to teach and train, building human connection into everything we do, and delivering tailored learning experiences that are meaningful and measurable. We are a fast-growing company with a passion for education and technology.

Position Overview

As we continue to expand, CYPHER Learning is looking for a dynamic and results-driven Sales Executive to focus on small business accounts (up to 350 employees). This role is ideal for a self-motivated sales professional who excels at outbound prospecting, lead qualification, and closing deals. If you have a hunter mentality and a passion for driving revenue through proactive sales efforts, we’d love to hear from you.

As an Account Executive for Small & Medium Size Businesses Accounts (AE, SMB), you will play a crucial role in growing our customer base. This position requires a strong focus on outbound prospecting, lead qualification, and managing the full sales cycle for small business accounts. Additionally, you will support enterprise-level lead qualification by identifying high-value opportunities for the Account Executive (AE) team in your assigned territory.

Key Responsibilities:

Prospecting & Lead Generation

• Conduct high-volume outbound prospecting through cold calls, emails, LinkedIn, and other channels to engage potential small business buyers.
• Research and qualify inbound and outbound leads to ensure alignment with CYPHER Learning’s ideal customer profile.
• Maintain a consistent pipeline of high-potential opportunities through strategic outreach and follow-ups

Sales Cycle Management (Small & Medium Business Accounts)

• Own the full sales cycle for small & medium business clients from initial contact to closing deals.
• Conduct engaging product demonstrations tailored to small business needs.
• Educate prospects on CYPHER Learning’s value proposition, ROI, and business impact.
• Negotiate pricing and contracts while maintaining a consultative, customer-first approach.
• Ensure a smooth transition for new clients by collaborating with the Customer Success team.

Enterprise Lead Qualification

• Qualify high-value enterprise leads and set up meetings for Account Executives.
• Collaborate with marketing and sales leadership to optimize lead conversion strategies.
• Maintain and update CRM (HubSpot/Salesforce) to ensure accurate tracking of pipeline activity.

Skills & Experience:

• 3-6 years of sales experience in an SDR, BDR, Inside Sales, or similar role, preferably in SaaS or EdTech.
• Proven track record of prospecting, qualifying leads, and closing sales in a B2B environment.
• Strong ability to cold call, personalize outreach, and handle objections effectively.
• Experience conducting discovery calls, product demos, and closing deals with small businesses.
• Proficiency with CRM systems (Salesforce, HubSpot, or similar) and sales automation tools.
• Excellent communication, negotiation, and presentation skills with a consultative approach.
• Self-driven, adaptable, and thrives in a fast-paced sales environment.

Bonus Skills:

• Experience selling LMS, e-learning, or SaaS solutions.
• Familiarity with account-based sales strategies for engaging larger accounts.
• Previous success in a quota-carrying role with a history of meeting or exceeding targets.