Role Description The Global Director of Sales Development will build, enable, and scale a world-class outbound revenue engine. This leader owns the global SDR strategy, performance, technology, and measurable pipeline contribution across all regions. This is a revenue ownership role, not an activity-management position. The primary mandate is to drive outbound-sourced revenue, with clear accountability to pipeline generation, conversion performance, and closed-won impact. Reporting to the SVP of Global Sales, this role partners closely with Marketing, RevOps, Enablement, and Regional Sales Leaders to ensure outbound is predictable, data-driven, and continuously optimized for scale. What will you do? - Process & Playbooks: Leverage AI to dynamically adapt playbooks based on real-time intent, ensuring the team isn't just following a static, manual script to drive measurable productivity improvements. - Build & Lead: Lead, mentor, and develop a world-class global Sales Development team with clear performance expectations and career pathways. - Strategy & Execution: Define and own the global inbound and outbound Sales Development strategy aligned with quarterly and annual revenue goals to help increase pipeline amounts, win rates, and reduce CaC. - Pipeline Ownership: Drive SDR-sourced pipeline targets with accountability for quality, conversion, and ARR impact, not just activity volume. - Be Technology Forward: Champion modern outbound tooling, including sequencing platforms, AI-driven personalization, intent data, and automation. - Use data and analytics to refine targeting, messaging, and performance management. - Continuously evaluate emerging technologies to increase scale without proportional cost growth. - Cross-Functional Alignment: Partner with Marketing, Field Sales, Enablement, and RevOps to streamline lead motion, optimize routing, and increase conversion efficiency. - Data & Forecasting: Own forecasting, capacity planning, performance modeling, and analytics to inform decisions and fuel continuous improvement. - Coaching & Development: Develop SDR managers as operational leaders who understand both sales economics and how to leverage new tools and trends, and people-first coaching. Qualifications - 7+ years of experience in Sales Development or Revenue leadership within B2B SaaS environments. - 3+ years leading global SDR teams. - Demonstrated success scaling outbound programs that generate significant revenue impact. - Strong operational leader with a deep understanding of pipeline economics, CAC, and conversion metrics. - Highly tech-forward, with hands-on experience implementing modern sales technologies and AI-driven workflows. - Data-driven, with the ability to build dashboards, forecasts, and performance models to guide decision-making. - Experience leading multi-region teams across North America and EMEA. What will give you an edge? - Experience leading SDR organizations of 30+ reps across multiple geographies. Benefits - Monthly Lifestyle subsidy: Use this for financial, physical, and mental well-being. - WFH set-up allowance: To ensure you have the right environment to work in, we will help you get set up within your first 3 months at UpGuard. - $1500 USD annual Learning & Development allowance: To support your career development, all team members will be able to expense development opportunities against this allowance. - Annual leave: PTO plus two additional UpGuardian leave days to give you time to recharge your batteries. - 18 weeks paid Parental Leave: Irrespective of parenting role. - Personal Leave Allowance: This includes sick & carer’s leave. - Fully remote working environment: While we have physical offices in Sydney & Hobart, we do not mandate compulsory attendance. - Top-spec hardware: All team members will be provided with top-spec laptops for their role. - Generative AI subsidy: UpGuard provides paid subscriptions for all team members to access generative AI tools to support their work. - Health Insurance: Health, dental, and vision insurance.

Role Description Chegg Skills is building the next chapter of Chegg. We operate at the intersection of workforce upskilling, career mobility, and outcomes-driven learning. This role exists to build, scale, and lead the revenue engine that will define Chegg Skills’ growth. We are looking for a Head of Sales who is more than a sales manager. This is a strategic, operational, and hands-on leader who can design systems, drive performance, coach teams, and close meaningful deals while navigating ambiguity. What You’ll Own - Revenue Strategy & Growth - Build and execute a clear sales strategy aligned to company growth goals - Identify opportunities across markets, verticals, and channels - Develop prospecting and closing strategies across: - Direct B2B - Channel partners - Government - Higher education - Workforce and enterprise buyers - Translate market insight into revenue action - Sales Operations & Process Excellence - Design and implement scalable sales processes, playbooks, and operating rhythms - Own pipeline management, forecasting, and sales velocity metrics - Build systems that drive consistency, clarity, and performance - Establish clear performance standards and accountability frameworks - Create processes that connect Sales with Product, Marketing, Operations, Engineering, and Leadership - Team Leadership & Culture - Build and lead a high-performing, low-ego sales organization - Set the tone for culture, execution, and accountability - Lead daily standups, pipeline reviews, and deal strategy sessions - Facilitate deal swarms for high-value opportunities - Step into deals when needed and coach in real time - Develop talent through ongoing training, coaching, and performance management - Strategic Partnership - Partner closely with the Head of Marketing to align demand generation and revenue execution - Serve as a trusted consultant to leaders across the organization - Translate business priorities into clear sales motions and outcomes - Bring a revenue perspective to company-wide decisions - Execution in Ambiguity - Operate effectively in an environment that combines startup speed with enterprise complexity - Build structure where needed without slowing momentum - Make smart decisions with imperfect information and adjust quickly - Balance long-term strategy with immediate execution Qualifications - You are not just a sales leader. You are a builder and architect of revenue systems. - Proven track record of building and scaling sales organizations - Deeply data-driven and detail-oriented - Experience designing sales processes, playbooks, and operating models from the ground up - Comfortable in strategy conversations and live deals - Understand GTM across multiple channels and buyer types - Skilled at coaching, training, and elevating sales talent - Respected as both a leader and a partner - Thrive in fast-moving, ambiguous environments - Scrappy, resourceful, and execution-focused Requirements - A clear, repeatable, and scalable sales process exists across the organization - The pipeline is healthy, predictable, and aligned to revenue goals - Sales velocity, conversion, and deal quality improve consistently - The sales team is coached, confident, and accountable - Marketing and Sales operate as true partners - Product and other teams have strong feedback loops from the market - Revenue becomes a function of system strength, not individual heroics Benefits - Comprehensive benefits plan for eligible employees, including: - Medical, dental, vision, life and supplemental life insurance - Short-and long-term disability - Mental health support - Parental leave - Paid time off - Paid holidays - 401(k) with matching contributions - Flexible Spending Account (FSA) and Health Savings Account (H.S.A.) options - Employee Stock Purchase Plan

Role Description Dearest Care has established strong demand for its high-touch, AI-powered patient advocacy model in the direct-to-consumer market. Our next phase is focused on driving repeatable B2B growth by partnering with health systems, IDNs, regional provider groups, and adjacent care delivery organizations. We are seeking a senior, hands-on seller to help secure our first major contracts in this space. This is not a traditional management role. We want a self-starter who can independently source opportunities, navigate complex enterprise sales cycles, structure pilots, address internal blockers, and close deals. You’ll work directly with the founders to define and build our sales process from the ground up. What You’ll Do - Own the end-to-end sales cycle with providers: prospecting, discovery, pilot/POV design, stakeholder alignment, procurement, security review, contracting, and close - Independently build your pipeline: create account lists, initiate outreach, follow up, and schedule meetings - Target and win regional health systems, IDNs, large medical groups, and other provider organizations - Design thoughtful pilots with clear success metrics, stakeholder maps, workflows, and conversion plans - Navigate multi-stakeholder buying environments involving clinical, operational, financial, legal, IT, and procurement leaders - Collaborate with founders, product, and operations teams to refine messaging, package outcomes, and optimize our enterprise offering - Transform early wins and setbacks into a repeatable sales playbook (ICP, personas, objection handling, pilot templates, deal process) Qualifications - Have personally closed complex provider-side deals with health systems, IDNs, hospital networks, medical groups, or care delivery organizations - Built pipeline from scratch without strong brand pull, SDR support, or mature marketing resources - Structured pilots or proof-of-value programs that directly led to signed contracts - Sold into multiple stakeholders, including clinical, operational, and financial buyers - Navigated long enterprise sales cycles involving procurement, legal, security, and internal politics - Thrived in fast-paced, ambiguous startup environments where speed and ownership matter Bonus if you: - Have experience in care coordination, patient navigation, care management, transitions of care, population health, or value-based care - Are familiar with Medicare Advantage - Have strong relationships with provider-side executives or decision-makers - Have successfully positioned offerings seen as overlapping with internal teams as complementary What Success Looks Like in 12 Months - First provider contracts signed and implementation launched - 1–2 well-defined pilots converted into commercial agreements - Established, repeatable early sales motion for provider partnerships - Demonstrated operational and clinical value with strong customer proof points - Clear momentum to scale provider GTM beyond founder-led sales Why Join Us - Work directly with founders on one of the company’s most critical growth drivers - Influence product, GTM, and enterprise strategy in real time - Ownership and accountability for scaling Dearest Care's B2B platform - Join a high-energy team committed to fast, impactful execution - Help close a $60B+ healthcare navigation gap with a proven model backed by investors and payers - Directly impact our success in winning major contracts in the next 12 months - Be part of a high-trust, mission-driven, patient-first culture How to Apply - Submit your résumé or LinkedIn - Include a brief note describing a deal you personally closed into a health plan or health system, highlighting what made it successful Our Vision & Culture We envision a future where every American has access to a personal healthcare navigator. Our platform democratizes healthcare navigation, unlocking vital services for individuals often left to navigate complex medical systems alone. We value diverse perspectives and operate primarily within the Americas timezone. Excellence, integrity, and conscious leadership shape our every decision. - Prioritizing human connection within our team and in our work - Pursuing excellence in execution, communication, and creative problem solving - Practicing radical candor—addressing tough topics with honesty and empathy, uplifting each other - Competing smartly in the customer’s interest - Upholding the 15 commitments to conscious leadership

Role Description The Director of Sales is an individual contributor responsible for driving new business revenue for IES within target industries. This person sells EOR (Employer of Record) and AOR (Agent of Record) workforce solutions to companies of all sizes, from emerging-growth businesses to mid-market and enterprise accounts. The role is built around two core activities: - Working an existing professional network to surface and convert opportunities. - Disciplined outbound prospecting to develop new client relationships where no prior connection exists. This person runs their own pipeline from first contact through contract close. Qualifications - 10+ years of direct sales experience, with at least 3 years selling workforce solutions, EOR/AOR, staffing, HR outsourcing, or related services. - Demonstrated track record of building pipeline from scratch - not just managing assigned accounts or converting inbound leads. - Proven ability to sell across deal sizes, from smaller growth companies through large enterprise accounts, adjusting approach based on buyer maturity and complexity. - Active professional network within the contingent workforce industry with a documented history of converting relationships into revenue. - Experience selling EOR, AOR, PEO, or contingent workforce solutions is strongly preferred. - Familiarity with the regulatory landscape around co-employment and worker classification is a plus. - Comfortable navigating multi-stakeholder sales cycles and presenting to HR, Finance, Legal, and C-level audiences. - BA/BS Degree in Sales, Marketing, Business, or equivalent work experience. - Understanding of staffing industry, contingent workforce, and contract service is a must. - Familiarity with EOR/AOR workforce solutions within the contingent workforce industry is required. - Proven success in winning business through RFP responses and presentations. - Proficient in Microsoft Office products. - CRM knowledge - uses it as an active pipeline management tool, not just a documentation system. Requirements - Build and manage a qualified pipeline of prospective clients within key sectors (including Software/Technology, Gaming, Defense, and Professional and Financial Services). - Activate existing professional relationships to generate referrals, introductions, and early-stage pipeline. - Prospect net-new relationships through direct outreach, industry events, trade associations, and conference participation. - Run a complete sales cycle - discovery, needs assessment, proposal, negotiation, and close - maintaining urgency without sacrificing client fit. - Identify the right buyer within each target account (HR, Finance, Operations, C-suite) and tailor the approach to the audience. - Conduct discovery sessions to understand each prospect's workforce structure, compliance exposure, and growth trajectory, then match those needs to IES service offerings. - Achieve quarterly and annual sales targets. - Prepare proposals, RFP/RFI responses, presentations, and contracts calibrated to client size and complexity. - Negotiate and execute service agreements in collaboration with Corporate Counsel to manage risk appropriately. - Work closely with Client Delivery/Operations and Finance to ensure a smooth implementation upon sale. - Maintain accurate, up-to-date pipeline data and activity records in CRM. - Serve as a credible voice on EOR and AOR models, contingent workforce trends, employment law considerations, and joint employer liability. - Represent IES at relevant industry events, trade forums, and professional networks within the target vertical. - Provide field-level intelligence on competitive dynamics, prospect objections, and market trends to inform IES strategy. - Stay current on employment law issues and joint employment liability. Company Description