Sales Development Representative - Microsoft 365 + Guardian (Tier-1 CSP)
About The Position
The Sales Development Representative (SDR) is the front edge of our sales engine. You will identify prospective mortgage, banking, credit union, and healthcare-practice customers, run initial outreach, qualify interest, and book demos for our Account Executive team. You will also follow deals through to close, coordinating between prospects, our Account Executive, our technical lead, and our CEO, so the relationships you start become customers you can point to. You do not need to have ten years of B2B SaaS experience. You need to be hungry, coachable, and good with people. We will teach you Microsoft 365, Microsoft 365 Copilot, and our Guardian product line. We will give you a sales playbook and pair you with experienced AEs and technical leads. What we cannot teach you is the discipline of following up. Every lead, every meeting, every introduction. That is the single biggest determinant of who succeeds in this role. The SDR also participates in our Value Catalyst compensation track: when you materially help an AE close a deal you sourced or supported, you share in the commission. This is how the role grows into bigger earnings as you build trust with the AE team and demonstrate that your introductions convert.
Requirements
- 1 to 3 years of sales experience in any B2B role: SDR, BDR, inside sales, account management, retail B2B, or a customer-facing role with a quota component.
- Ability to show a CRM, spreadsheet, or notebook where you ran a follow-up cadence and stuck to it.
- Comfortable with rejection.
- Ability to build a system to come back to prospects who say 'let me think about it'.
- Treat a prospect as someone to build trust with, not as a transaction to close.
- Ability to write a clear, concise follow-up email, and actually send the ones you said you would.
- Ability to run a 15-minute qualifying call and end it with either a booked demo or a clean 'not now' plus a follow-up trigger.
- Communicate well in writing and on calls, comfortable with executives and IT decision-makers.
- Coachability: willingness to learn our sales playbook and Microsoft product universe with work ethic and curiosity.
- Work independently with high accountability, follow-through, and time management.
- Comfortable using HubSpot (preferred) and modern sales tools.
- Collaborate well with the AE team, our technical lead, and leadership.
Nice To Haves
- Any Microsoft 365 or Office exposure (Office admin, Help Desk, IT, systems support)
- Mortgage industry background (loan officer, processor, underwriter, mortgage tech sales, LOS support)
- Healthcare practice background (medical-device or EHR sales, practice admin, dental, behavioral health)
- A demonstrated track record in any role of patient, methodical relationship building over time
Responsibilities
- Build outbound pipeline through calls, email sequences, LinkedIn outreach, and referrals into mortgage companies, credit unions, community banks, and healthcare practices.
- Qualify inbound leads from our website, content campaigns, and partner referrals, separating the genuinely interested from the curious.
- Book qualified demos for our Account Executive team.
- Follow up like clockwork: every prospect, every meeting, every introduction.
- Own daily activity in HubSpot CRM.
- Coordinate calendar logistics between prospects and our team.
- Learn the Guardian product line from our technical lead so you can talk credibly about how Microsoft 365, Copilot, and Guardian come together.
- Pivot between mortgage and healthcare prospects as the healthcare vertical scales.
Benefits
- Competitive base salary
- Value Catalyst commission share on deals you source and substantially support
- Activity-based incentives tied to qualified demos booked and converted to AE opportunities
- Target Year 1 OTE: $80,000 to $100,000 (base + commission combined)
- 401(k) with employer matching
- Defined growth path into Senior SDR or Account Executive roles
- 100% employer-paid medical insurance for employees
- Dental coverage
- Vision coverage
- Generous paid time off
- Paid holidays
- Microsoft 365 fundamentals training and certification support (MS-900 at minimum within Year 1)
- Mentorship from experienced Account Executives
- Exposure to mortgage, financial services, and healthcare verticals
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
