Mid-Market Account Manager

Jobtailor; New York (NY); On-site; USD 100,000 - 160,000; Full time

Job summary

Jobtailor in New York seeks a senior Account Management/Customer Success professional to own a Mid-Market portfolio for renewal and expansion. You will partner with CS managers to execute strategic account plans, uncover business needs, and drive revenue through upsells and cross-sells.

You will build executive-level relationships across Operations, IT, Finance, and HR, translating capabilities into measurable ROI and workforce optimization outcomes.

Qualifications

• 5+ years of experience in B2B SaaS, including Account Management or Customer Success with revenue ownership.
• Demonstrated experience managing and growing Mid-Market customer relationships.
• Track record of driving renewals, expansion, upsells, or cross-sells.
• Strong discovery skills and ability to uncover underlying business problems.
• Commercial judgment and comfort navigating pricing, contracts, negotiations, and procurement.
• Executive presence and ability to communicate with senior leaders and day-to-day users.

Responsibilities

• Own the commercial relationship for a portfolio of Mid-Market customers.
• Partner with Customer Success Managers to execute account plans covering stakeholders, priorities, risks, whitespace, and expansion opportunities.
• Drive renewals and proactively identify opportunities to grow MRR.
• Expand Insightful across teams, departments, geographies, products, and use cases.
• Build and maintain an expansion pipeline.
• Forecast renewals and expansion opportunities accurately.
• Develop customer business, operating model, priorities, and challenges knowledge.
• Build relationships with senior leaders across Operations, IT, Finance, HR, Transformation, and other functions.
• Lead discovery conversations and executive business reviews focused on outcomes, ROI, priorities, and next steps.
• Connect Insightful's capabilities to measurable outcomes including productivity, operational efficiency, workforce optimization, AI transformation, and automation.
• Communicate complex ideas simply and help customers build internal business cases for expansion.
• Help customers understand how workforce data supports operational improvement, process redesign, AI, and automation.
• Partner with product and technical teams to bring capabilities into accounts and shape go-to-market strategy

Skills

Account Management

Customer Success

Renewals

Expansion

Upselling

Cross-Selling

Discovery Skills

Commercial Judgment

Negotiation

Detail Orientation

Executive Presence

Communication

Curiosity

Relationship Building

Adaptability

Mid-Market

Customer Relationships

Operational Improvement

Process Redesign

Automation

Tools

Workforce Technology

Analytics

AI

HR Technology

Productivity Software

Enterprise SaaS

Job description

• Own the commercial relationship for a portfolio of Mid-Market customers


• Partner with Customer Success Managers to execute account plans covering stakeholders, priorities, risks, whitespace, and expansion opportunities


• Drive renewals and proactively identify opportunities to grow MRR


• Expand Insightful across teams, departments, geographies, products, and use cases


• Build and maintain an expansion pipeline


• Forecast renewals and expansion opportunities accurately


• Develop customer business, operating model, priorities, and challenges knowledge


• Build relationships with senior leaders across Operations, IT, Finance, HR, Transformation, and other functions


• Lead discovery conversations and executive business reviews focused on outcomes, ROI, priorities, and next steps


• Connect Insightful's capabilities to measurable outcomes including productivity, operational efficiency, workforce optimization, AI transformation, and automation


• Communicate complex ideas simply and help customers build internal business cases for expansion


• Help customers understand how workforce data supports operational improvement, process redesign, AI, and automation


• Partner with product and technical teams to bring capabilities into accounts and shape go-to-market strategy

Requirements

• 5+ years of experience in B2B SaaS, including Account Management, Customer Success with commercial ownership, or a similar customer-facing revenue role


• Demonstrated experience managing and growing Mid-Market customer relationships


• Track record of driving renewals, expansion, upsells, or cross-sells


• Strong discovery skills and ability to uncover underlying business problems


• Commercial judgment and comfort navigating pricing, contracts, negotiations, and procurement


• Executive presence and ability to communicate with senior leaders and day-to-day users


• Strong business acumen and genuine curiosity about how companies operate


• Ability to manage multiple opportunities and priorities without losing attention to detail


• Comfort operating in a fast-moving, evolving environment


• Experience with workforce technology, analytics, AI, HR technology, productivity software, or enterprise SaaS is a plus, but not required

Core Competencies

Demonstrates expertise in managing Mid-Market customer relationships, driving renewals, and identifying expansion opportunities. Possesses strong business acumen and the ability to communicate effectively with senior leaders while navigating complex commercial environments.

Highest-signal resume keywords

• B2B SaaS Experience


• Account Management


• Customer Success


• Renewals and Expansion


• Business Acumen

Hard Skills

• Account Management


• Customer Success


• Renewals


• Expansion


• Upselling


• Cross-Selling


• Discovery Skills


• Commercial Judgment


• Negotiation


• Detail Orientation

Soft Skills

• Executive Presence


• Communication


• Curiosity


• Relationship Building


• Adaptability

Industry Keywords

• Mid-Market


• Customer Relationships


• Operational Improvement


• Process Redesign


• Automation

Tools & Technologies

• Workforce Technology


• Analytics


• AI


• HR Technology


• Productivity Software


• Enterprise SaaS