Account Executive - Mid Market

Big Time Software is offering a unique opportunity to join our dynamic sales organization as an Account Executive. In this role, you’ll be responsible for managing and expanding a portfolio of high-potential accounts by delivering measurable business outcomes through our industry-leading professional services automation (PSA) platform.

This is a strategic, full-cycle sales role—not a transactional one. You’ll work cross-functionally with internal teams, serve as a trusted advisor to your prospects, and lead consultative sales engagements that align Big Time’s solutions with real customer needs.

You’ll draw on your product knowledge and sales acumen to uncover business and technical requirements, delivering tailored solutions that highlight Big Time’s value. Join a collaborative, high-performing team in a fast-paced environment where multitasking, creativity, and curiosity are valued. As a key driver of our mid-market growth strategy, you’ll have high visibility, ownership, and the opportunity to make a meaningful impact—while accelerating your career in SaaS sales using the latest AI technologies to find efficiencies.

Big Time Software is the AI-powered professional services platform enabling intelligent decisions and delivering profitable growth. We've proudly been featured on Inc's 500 Fastest Growing Companies in America for 4 years in a row. Big Time Software is the engine behind the greatest consulting firms on the planet, delivering back-office time/budgeting and invoicing to over 2,700 firms worldwide and tracking over $4 billion in billable time each year.

Our flagship product is a SaaS-based system that is custom-built for the professional services industry.

Big Time is a PE-backed company, headquartered out of Chicago, with offices in Chicago, Phoenix and Poland. We've proudly been named on Crain’s “Best Places to Work” three years in a row -- if you're motivated to join a hyper growth organization, we're eager to talk to you.

• Competitive salary and bonus.

• Company pays 100% of benefits, including medical, dental, vision, disability and life insurance.

• 401k with generous company match.

• Hybrid work schedule
  - In office 3 times a week.

• Generous time off and paid company holidays.

• Paid Parental Leave

• Fresh fruit, snacks, cold brew coffee/tea, soda and sparkling water.

• Latest AI-powered tech stack & tooling.

• Onsite gym.

• Own and drive the full sales cycle: prospecting, qualification, demo, proposal, negotiation, and close to ensure a seamless & impactful buying journey.

• Develop deep knowledge of Big Time’s product offerings and articulate business value to our prospects, ranging from C-suite level executives, Operations leaders, Project Management leaders & more.

• Strategically build and maintain a healthy pipeline to exceed quota through proactive outreach and inbound lead management, using AI tooling to accelerate.

• Conduct consultative discovery calls to uncover customer pain points, workflow gaps & processes and long & near-term firm objectives.

• Use AI to create & maintain collateral to power your deal processes; partnering with Content Marketing & Product Marketing teams internally to create a best-in-class experience for your prospects.

• Strategize using AI + Solutions Consultants to prepare a tailored and impact demo experience for your prospects, leaning on your deep product & industry expertise to guide value-based conversations.

• Build strong, lasting relationships with customers, becoming a key point of contact and trusted partner.

• Collaborate cross-functionally with Solutions Consultant, Customer Success, Marketing, and Product to deliver a seamless buying experience.

• Stay up to date with industry trends, competitors, and Big Time’s evolving product roadmap.

• 4+ years of quota-carrying experience in B2B SaaS, preferably in a consultative or complex sales environment

• Experience managing mid-market accounts with strategic, multi-stakeholder sales cycles

• Comfortable engaging and influencing C-level executives and business decision makers

• Proven ability to deliver value-based, solution selling and ROI-based messaging

• Exceptional…