Account Executive - Mid Market

Mid-Market Account Executive
Chicago, IL (Hybrid - 3 days/week in office preferred)
BigTime Software is seeking a Mid-Market Account Executive to drive new business within our strongest customer segment: professional services firms with 20-100 employees. This is a full-cycle sales role responsible for prospecting, discovery, running your own initial demos, and closing deals. While the segment has healthy inbound volume, success requires meaningful outbound pipeline creation, strong sales fundamentals, and a consultative approach. As a key contributor to our mid-market strategy, you'll work cross-functionally, influence product adoption, and help firms solve operational challenges through BigTime's PSA platform.
About BigTime
BigTime Software is the AI-powered professional services platform enabling intelligent decisions and profitable growth. Featured on Inc.'s 500 Fastest Growing Companies four years in a row and named a Crain's Best Place to Work for three consecutive years, BigTime powers 2,700+ consulting, AEC, accounting, IT services, and agency firms-tracking over $4B in billable time annually. Our flagship SaaS product is purpose-built for project-based, billable organizations that require visibility into utilization, staffing, project margins, invoicing, and firm-wide operational health.
What You'll Do
• Manage the full sales cycle: outbound prospecting, qualification, discovery, self-led demos, proposal, negotiation, and close
• Develop expertise in BigTime's platform and communicate value to C-suite, finance, operations, and project management leaders
• Build and maintain a 3x pipeline through a mix of inbound lead management and proactive outreach
• Conduct consultative discovery to uncover pain points around utilization, project margins, invoicing workflows, staffing, and forecasting
• Collaborate with Solutions Consultants to tailor demos and deal strategy
• Use AI tools to optimize outreach, messaging, and deal management
• Partner with Marketing, Product, Customer Success, and Sales Leadership to deliver a seamless, value-driven buying experience
• Stay informed on competitive trends and BigTime's evolving product roadmap
Who You Are
• 4+ years of full-cycle, quota-carrying B2B SaaS experience
• Experience selling into SMB/mid-market organizations; professional services vertical experience strongly preferred
• Proven ability to run your own demos, lead consultative sales cycles, and manage multi-stakeholder deals
• Comfortable selling ACVs typically in the $17k-$30k range
• Able to clearly articulate your sales metrics: quota, attainment, ACV, pipeline contribution, close rates
• Strong communicator capable of engaging C-level and business decision makers
• Highly self-directed with excellent time management and follow-up discipline
• Collaborative teammate who thrives in a hybrid, fast-paced environment
• Proficient with Salesforce; experience with PSA, ERP, or accounting platforms (QuickBooks, Intacct) is a plus
• Must be authorized to work in the United States. We do not offer sponsorship now or in the future.
What We Offer
• Competitive salary & bonus
• 100% company-paid medical, dental, vision, disability, and life insurance
• 401(k) with generous company match
• Hybrid schedule (3 days/week in office)
• Generous PTO & paid company holidays
• Paid parental leave
• Fresh fruit, snacks, cold brew & sparkling water
• Latest AI-powered tooling & sales technology
• Onsite gym (Chicago HQ)
Compensation
Base salary range: $80,000-$95,000 plus variable compensation. Actual earnings will depend on experience, skills, and sales performance. Additional compensation may be available based on quota attainment and overachievement.
Equal Opportunity
Applicants must be authorized to work in the U.S. BigTime Software, Inc. is proud to be an Equal Opportunity Employer. We do not offer work authorization sponsorship.