Senior Account Executive

Sales - Senior Account Executive

Location: Cleveland or Columbus, OH (Remote with local travel)

About the Role

We need a Senior Account Executive who can open doors, close deals, and build lasting client relationships in the Microsoft services space. You'll own the full sales cycle—prospecting, discovery, scoping, proposal, negotiation, and close—for mid-market and enterprise clients who need help maximizing their Microsoft investments across Microsoft 365, Azure, Entra ID, Defender, Purview, and Copilot. You'll bring your own network, hunt new relationships, and convert technical problems into signed SOWs. If you've sold IT professional services in the Microsoft ecosystem, you understand the difference between a $50K quick-win project and a $500K multi-phase engagement, and you know how to structure both.

What You'll Do

Sales Execution: Own a $2M–$3M annual quota in net new business (companies we have not signed an SOW with before). Prospect and close deals across mid-market and enterprise accounts in your local market (Cleveland or Columbus). Run the full sales cycle: initial outreach, discovery calls, technical scoping with our team, proposal development, negotiation, and contract signature. Build pipeline through your existing network, referrals, and direct outreach (this is a relationship-based business, and you should come with one). Manage opportunities in CRM and forecast your pipeline accurately.

Client Relationship Management: Serve as the primary relationship owner for accounts you bring in (you own the land, but delivery and account management are handled by our team). Identify upsell and expansion opportunities within your accounts and hand them to the appropriate team member. Act as the client's advocate internally when issues arise, but your primary focus is hunting new logos.

Technical Discovery & Scoping: Conduct discovery calls to uncover the client's technical environment, pain points, and desired outcomes. Partner with our leadership team for technical validation, architecture discussions, and solution design during the sales process. Translate technical requirements into clear SOWs that set realistic expectations and protect both parties.

Market Presence: Represent Company at local industry events, user groups, and client meetings. Build and maintain relationships with referral partners: MSPs, VARs, Microsoft sellers, and peer consultancies. Travel locally for face-to-face meetings, lunches, and relationship-building.

What We're Looking For

Sales Experience: 5+ years of B2B sales experience selling IT professional services, consulting, or managed services. Proven track record closing $1M+ in annual revenue, with deal sizes ranging from $50K to $500K+. Deep familiarity with the Microsoft ecosystem: Microsoft 365, Azure, Entra ID, Exchange, Teams, SharePoint, Intune, Defender, Purview, Copilot, and related technologies. Experience selling to IT leaders (CIOs, IT Directors, IT Managers) in mid-market and enterprise organizations. Ability to articulate technical value without needing to be the technical expert.

Relationship & Pipeline Development: Existing network of IT decision-makers in Cleveland or Columbus (or the ability to build one quickly). Track record of generating your own pipeline through networking, referrals, and outbound prospecting. Comfortable working in a referral-based, relationship-driven business where trust and reputation matter more than cold calls.

Sales Skills: Strong discovery skills: you know how to ask the right questions to uncover pain, budget timeline, and decision-making authority. Ability to structure complex, multi-phase engagements and translate them into clear proposals. Negotiation skills: you know when to hold firm, when to flex, and how to close without leaving money on the table. Pipeline discipline: you keep HubSpot clean, forecast accurately, and know where every deal stands at all times.

Preferred (Nice to Have): Experience selling Microsoft security, compliance, or identity services (CMMC, NIST, CIS benchmarks, Zero Trust). Familiarity with Microsoft partner programs and co-selling with Microsoft account teams. Existing relationships with MSPs, VARs, or other referral sources in the Ohio market.

Quota: $300K ($2M–$3M quota × 10%) This is one of the most aggressive commission structures in the industry because we want someone who can sell.

Schedule: Monday–Friday with flexibility to attend evening events, client dinners, or breakfast meetings when needed. Local travel required for face-to-face meetings—this is a relationship business, and you should expect to be out of the house regularly. Remote work is supported, but you need to be in-market (Cleveland or Columbus) to build the relationships that matter. Most importantly, you'll need to embrace our culture of ownership – which means sometimes doing things that aren't technically "your job" because it's the right thing to do.

Why Work With Us

Benefits: Health Insurance options including Medical, Dental, Vision Flexible Time Off Policy and Company-wide Holidays 401k with 6% employer match (both traditional and Roth) Paid volunteer opportunities Professional Development: Paid training, certifications, and annual development budget

Why Join Us?

We are defined by the people in this company, so it's important that everyone shares a set of core values:

Ownership

This is the root of everything we do. It means taking complete responsibility for everything within your sphere of influence, regardless of circumstances or external factors. It means never blaming others, making excuses, or pointing fingers.

Humility

We approach every engagement knowing we don't have all the answers. We listen more than we speak, learn from our clients and teammates, and remain open to being wrong.

Discipline

We do what we say we'll do, when we say we'll do it. We maintain rigorous standards in our work, communications, and commitments.

ROTA

Relationships over transactions; always. We are in a relationship-based business, and our success depends on our clients' success. Respects and trusts the expertise and judgment of our team. We empower them to do what they think is right. We also work collaboratively. We always look for the right amount of structure and unity necessary to maximize productivity. Where it makes sense, we designate someone to make a call. Our team is small and growing, and we frequently operate in cross-functional teams depending on the project, so you'll get to work with awesome people from all different roles and technical backgrounds in the company. Regardless of their varied interests, all of our team members have one thing in common: They are great to work with. We believe in ownership and leading with empathy, and are always looking to improve how we do things. We all love to program and solve problems in creative ways, and we regularly take time to geek out and show each other something cool we built or found to make our lives easier. Last but not least, we take investing in our team and their goals seriously. We provide advancement opportunities, including advanced engineer roles, Team Lead, and Solutions Architect positions, and make sure you have access to training, certifications, and coaching to get the most out of our career here.