Mid-Market Account Executive

Field sales powers the economy — but most teams are struggling. Reps are buried in admin work, managers are stretched thin, and leaders can’t see what’s really happening in the field.

Siro is redefining how field sales teams learn, perform, and win.

We started as an AI-powered coaching platform that helped reps improve their outcomes in the field.

Today, we’re something much bigger — an intelligent companion that automates sales reps’ tedious admin work, gives managers real-time visibility, and helps executives see around corners.

Our platform integrates with systems like Salesforce, analyzing thousands of in-person sales conversations to surface insights, automate workflows, and drive better outcomes across the org. Think Iron Man’s Jarvis for sales — proactive, personalized, and built directly into the tools teams already use.

Siro has raised $75M and is backed by world-class investors like Index, Fika, CRV, and SignalFire. We are trusted by leading home-improvement, retail, hospitality, and automotive brands, and powered by a lean team from Meta, McKinsey, Doordash, and Uber.

We’re building the future of human-AI collaboration in sales — and we’re just getting started.

We are seeking an outstanding Mid-Market Account Executive who lives to hunt. This person will play a critical role in expanding our footprint among mid-market companies: identifying high-potential opportunities, breaking into new accounts, and building lasting relationships that drive revenue. You'll be a key member of our sales org, working closely with Marketing, Customer Success, Product, and Leadership.

• Develop and execute a strategy to source, pursue, and close new mid-market customers in target verticals (e.g., home improvement, retail, hospitality, automotive).

• Hunt new business: cold outreach (calls, emails, social), leveraging networks, referrals, events, etc.

• Own the full sales cycle from initial outreach through contract negotiation and signing.

• Build, maintain, and grow a pipeline of mid-market opportunities; forecast with accuracy and drive predictable revenue.

• Partner cross‑functionally: collaborate with Marketing to align on lead gen and content; with Product to feed customer insights; with Customer Success to ensure smooth onboarding and a strong handoff.

• Serve as a trusted advisor and subject matter expert: lead discovery and demo conversations, position the product compellingly, and act as the face of our mid-market go‑to‑market.

• Provide feedback to leadership on market trends, competitive intelligence, pricing, and packaging.

• 3-5 years of B2B SaaS sales experience, with a focus on hunting new logos and managing the full sales cycle.

• Proven track record of meeting or exceeding quota in a mid-market or SMB closing role.

• Ability to quickly build relationships with key stakeholders — from operations managers to VPs and owners — within target verticals.

• Experience selling to multiple personas across an organization, navigating buying committees without getting stuck.

• Strong ability to generate your own leads, build pipeline, and close deals with minimal hand-holding.

• Excellent communication skills; ability to run a tight discovery, tell a compelling story, and handle objections with confidence.

• Self‑motivated, highly organized, resilient; comfortable working independently in a fast-moving environment and figuring things out as you go.

• High ownership & impact: this isn't a support role — you'll own your book, your strategy, and your results.

• Fast‑paced, mission‑driven culture where ideas matter and you can see the difference you make.

• Competitive compensation package: base + variable (quota‑bearing), equity, and benefits.

• Opportunity to shape the future of field sales intelligence at a company that's redefining how sales teams learn and perform.

• Strong team culture: helpful, smart, ambitious, and collaborative.

At Siro, we are committed to creating a diverse and inclusive environment where all people feel that they are equally respected and valued, whether they are applying for an open position or working at the company. We provide equal employment opportunities to all applicants without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.