Strategic Sales Trainer (AI)

Location: New York, NY, United States; in-office role with the option to work remotely 20% of the month, or 4 days, when minimum performance standards are met.

Salary: $96,000–$132,000 base plus equity.

Company

hirify.global provides financial decision-making tools and helps small businesses access financing to start, grow, and succeed.

What you will do

• Design post-boot-camp coaching, reinforcement, skill assessments, development plans, and milestones for representatives in their first 12 months on the sales floor.
• Coach representatives to prioritize books of business, reengage inactive customers, uncover financing needs, develop relationship strategies, and generate repeat business.
• Strengthen renewal and lender conversations by evaluating financing history, obligations, eligibility, timing, financing structure, and customer needs.
• Improve personalized call, text, and email cadences, prospecting, follow-up, relationship building, and active-offer execution.
• Deliver live observation, call reviews, role plays, deal strategy sessions, and Challenger-based and consultative sales coaching.
• Build AI-powered role-play scenarios, customer profiles, coaching rubrics, feedback tools, and data-driven enablement programs; partner with Sales, Business Development, Product, Operations, and Learning & Development.

Requirements

• At least 2 years of experience in sales training, enablement, coaching, or frontline sales leadership within a fast-paced, quota-driven organization.
• Demonstrated success improving sales ramp and performance through structured development plans, live observation, call reviews, role plays, and actionable feedback.
• Experience selling to or coaching teams serving existing customers, including book-of-business prioritization, reengagement, renewals, and personalized multichannel outreach.
• Strong understanding of Challenger, consultative, and transactional sales methodologies.
• Excellent communication, facilitation, and relationship-building skills, with the ability to earn trust and deliver direct coaching.
• Experience with sales and enablement technologies such as Salesforce, conversational intelligence tools, sales engagement platforms, or learning management systems.
• Data-driven approach to identifying skill gaps and measuring coaching impact on customer engagement, sales behaviors, and business results.
• Comfort using AI tools and interest in developing AI-powered sales practice and feedback.
• Willingness to travel approximately twice per quarter for in-person onboarding, training, and coaching.

Nice to have

• Experience in small business financial services, alternative lending, MCA, fintech, or comparable high-volume transactional sales.
• Knowledge of repeat financing and positioning existing and alternative lenders.
• Experience building AI role-play scenarios, coaching rubrics, or AI-enabled development programs.
• Experience designing and optimizing outreach cadences for existing customers.
• Formal training or certification in Challenger, SPIN Selling, Sandler, MEDDICC, or a similar methodology.

Culture & Benefits

• In-person sales-floor collaboration with flexibility to work remotely 20% of the month when performance standards are met.
• Medical, dental, and vision coverage; mental health support; FSA and HSA plans; disability and life insurance.
• Flexible vacation time, 11 holidays, company shutdown, new-parent leave, and a paid sabbatical after 5 years.
• Wellness, cell phone, Wi-Fi, work-from-home equipment, and coworking stipends where applicable; remote-only stipends require remote eligibility.
• 401(k) with a 4% company match, financial wellness support, and access to a Certified Financial Planner through Northstar.
• Employee resource groups, hackathons, team events, volunteer time off, and charitable matching.

Hiring process

• Qualified applicants are considered under hirify.global’s equal opportunity hiring policy and applicable fair-chance laws.