BigTime Software
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.
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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.
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