Sales Director, Enterprise

Syndicate; Chicago, Northern (IL, KY); Hybrid; USD 120,000 - 160,000; Full time

Job summary

Syndicate in Chicago seeks a dynamic enterprise sales leader to manage and coach a team of Enterprise Account Executives covering the US market. This is not just a management role; you will lead from the front, help close deals, and raise the bar across the team.

You’ll drive pipeline, shape outbound and inbound motion, and partner with marketing on GTM initiatives targeting SMBs. Expect high ownership, fast decision lines, and equity in a fast-growing startup.

Qualifications

• Proven leadership of high-performing SaaS sales teams in enterprise segments.
• Experience managing Account Executives and coaching sales reps.
• Strong outbound sales, prospecting, CRM workflows, and pipeline management.
• Tech-savvy with ability to sell technical products.
• Exceptional coaching and people-management skills.
• Self-starter thriving in fast-growing startups.
• Ideally based in Chicago.

Responsibilities

• Lead, coach, and scale a team of ENT Account Executives.
• Drive pipeline generation and revenue growth across your territory.
• Improve outbound, inbound, and sales execution processes.
• Support reps on strategic deals and key accounts.
• Build a high-performance, high-accountability sales culture.
• Collaborate with marketing and growth on GTM initiatives targeting SMB customers.
• Hire, onboard, and develop top sales talent.
• Forecast accurately and manage team performance metrics.

Skills

Leadership of SaaS sales teams

Manage Account Executives

Outbound prospecting

CRM & pipeline management

Tech sales

Coaching & people management

Startup mindset

Tools

CRM systems

Job description

We’re making security suck less for developers.

Security tools haven’t kept up with how software is built today. They interrupt teams, slow releases, and turn security into a bottleneck instead of a capability. We built Aikido to change that. Aikido builds developer-first security products that reduce real risk without getting in the way of shipping software. We focus on what actually matters and automate the rest.

We’re taking on legacy security tools teams have been stuck with, and we’re winning. If you want to help us take market share and build products developers actually enjoy using, you’re in the right place.

Founded in 2022 by third-time founders, Aikido has $85M in the bank and a long runway ahead. We’re building toward self-securing software. Join an all-star team. Take real ownership. Push boundaries. Build things that matter.

You’ll be responsible for managing and coaching a team of Enterprise Account Executives covering the US market. This is not a pure management role; we're looking for someone who leads from the front, helps close deals, sharpens execution, and raises the bar across the team.

Responsibilities

• Lead, coach, and scale a team of ENT Account Executives

• Drive pipeline generation and revenue growth across your territory

• Improve outbound, inbound, and sales execution processes

• Support reps on strategic deals and key accounts

• Build a high-performance, high-accountability sales culture

• Collaborate with marketing and growth on GTM initiatives targeting SMB customers

• Hire, onboard, and develop top sales talent

• Forecast accurately and manage team performance metrics

• Proven experience leading high-performing SaaS sales teams in an enterprise segment

• Experience managing Account Executives

• Strong understanding of outbound sales, prospecting, CRM workflows, and pipeline management

• Tech-savvy and comfortable selling technical products

• Strong coaching and people management skills

• Self-starter who thrives in a fast-growing startup environment

• Ideally based in Chicago

What you can expect

• Short decision lines. Big ownership. Shape the projects that matter and ship fast.

• Grow as fast as we do. Take on more, own more, and carve out your own path.

• Top-tier tech pay and equity.

• High trust, strong values, zero corporate BS.

• Flexibility in working hours.

• A company that sticks to its values in an open and informal atmosphere.

We hire for talent, drive, and potential. Everything else is noise.