Mid-Market Account Manager

About Insightful

Insightful is transforming how companies understand, optimize, and automate work.

Our platform gives organizations visibility into how work actually happens across their teams helping leaders uncover inefficiencies, improve productivity, redesign workflows, and identify where AI and automation can have the greatest impact.

As we expand from workforce analytics into Work Intelligence, we're building a new category at the intersection of workforce data, operational intelligence, and AI.

We're growing quickly, and we're looking for a Mid-Market Account Manager to help us deepen and expand relationships with our customers.

Job Description

As a Mid-Market Account Manager, you'll own a portfolio of existing customers and be responsible for retention, expansion, and the overall commercial relationship.

This is not a reactive account management role.

We want someone who is curious about how businesses operate, can uncover problems customers may not yet know they have, and can translate those problems into meaningful business outcomes.

You'll build relationships across customer organizations - from day-to-day champions to executives - while identifying opportunities to expand Insightful's footprint through additional users, products, teams, and use cases.

You'll work closely with Customer Success, Solutions Engineering, Product, and Sales, but you'll ultimately own the commercial strategy and growth of your accounts.

Responsibilities:

Own & Grow Your Business

• Own the commercial relationship for a portfolio of Mid-Market customers
• Partner with Customer Success Managers on executing account plans that identify stakeholders, business priorities, risks, whitespace, and expansion opportunities
• Drive renewals while proactively identifying opportunities to grow MRR
• Expand Insightful across new teams, departments, geographies, products, and use cases
• Build and maintain a healthy expansion pipeline within your book of business
• Forecast renewals and expansion opportunities accurately

Become a Strategic Partner and Lead Executive Conversations

• Develop a deep understanding of each customer's business, operating model, priorities, and challenges and therefore relationships with senior leaders across Operations, IT, Finance, HR, Transformation, and other functions
• Lead meaningful discovery conversations rather than simply responding to customer requests
• Partner with Customer Success managers to conduct executive business reviews focused on outcomes, ROI, priorities, and what's next
• Connect Insightful's capabilities to measurable business outcomes, including productivity, operational efficiency, workforce optimization, AI transformation, and automation
• Communicate complex ideas simply, confidently, and commercially; help customers build the internal business case for expanding their partnership with Insightful

Bring Work Intelligence to Market

Insightful is evolving quickly, and our Account Managers play an important role in bringing new products and ideas to customers. You'll help customers understand how workforce data can move beyond reporting and answer bigger questions:

Where is work inefficient?

Which processes should be redesigned?

Where can AI or automation create leverage?

How can leaders measure whether those changes actually worked?

You'll partner closely with our product and technical teams to bring these capabilities into your accounts and help shape how we take them to market.

You are a great fit for this role if you have:

• 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.
• A track record of driving renewals, expansion, upsells, or cross-sells
• Strong discovery skills—you know how to ask good questions, follow the thread, and uncover the business problem underneath the initial request
• Commercial judgment and comfort navigating pricing, contracts, negotiations, and procurement
• Executive presence and the ability to communicate effectively with both 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 environment where the product, playbook, and organization are still evolving
• Experience with workforce technology, analytics, AI, HR technology, productivity software, or enterprise SaaS is a plus - but not required