Join to apply for the Director of Sales role at JOBS by allUP

A variety of soft skills and experience may be required for the following role Please ensure you check the overview below carefully. 2 days ago Be among the first 25 applicants Join to apply for the Director of Sales role at JOBS by allUP Get AI-powered advice on this job and more exclusive features. This range is provided by JOBS by allUP. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range $140,000.00/yr - $160,000.00/yr About our client Parento is the first provider for paid parental leave, distributing the first and only paid parental leave insurance and parental support program. Their holistic program enables companies to offer paid maternity and paternity leave to all employees. Designed to support working parents while alleviating HR’s workload, Parento’s white glove leave concierge handles the complexities of leave management, payroll calculations, compliance, and claims, while providing emotional and parent coaching for employees. Their proprietary program boasts a 95% return-to-work rate and guides employees through the process before, during, and after leave to ensure a seamless re-onboarding. About the role Parento is hiring a Director of Sales who is both a top‑tier closer and a builder of systems, people, and process. This is a player-coach role, responsible for owning key deals while mentoring a small team, creating stand up repeatable sales motions across direct and broker channels, and partnering tightly with Marketing to drive pipeline and learnings. This is a sleeves‑rolled‑up role reporting to the CEO. Responsibilities Own revenue: Prospect, run full‑cycle deals, and close new business while setting standards for discovery, demos, negotiation and forecasting Build the engine: Design and implement our sales strategy, operating cadence, and playbooks partnering with the broader team where necessary (e.g. ICP, messaging, qualification, pricing, proposals, and objection handling). Enable the sales team to close deals at market-leading rates. Scale the team: Recruit, onboard and coach the sales team; establish goals, enablement, and performance management. Broker & partner channels: Activate and grow benefits brokers and PEOs in partnership with our VP of Partnerships and Sales Consultants; create tiered engagement plans, trainings, and co‑marketing. Process & metrics: Stand up rigorous pipeline hygiene, stage definitions, and forecasting rhythm; create dashboards for conversion, win rates, sales cycle and channel ROI. A strong focus on results and outcomes is essential. Marketing partnership: Partner with Marketing to fully develop an integrated funnel from lead to close; run closed‑loop feedback on campaigns, content, and offers; share market intel and VOC. Cross‑functional leadership: Partner with the broader team and senior leadership on packaging, pricing, implementation readiness, and renewals/expansion. Compliance & credibility: Represent Parento with employers and intermediaries; maintain/obtain producer licensing (as needed). What Success Looks Like (first 6–12 months) 3–4x qualified pipeline coverage and accurate monthly forecasts. Documented sales playbooks and enablement assets in use across the team. Activated broker program with prioritized national/regional partners and repeatable co‑sell motion. Clear funnel benchmarks (MQL→SQL→Opportunity→Close) and improved conversion at 1–2 targeted stages. Detailed metrics and dashboards to document progress. Shortened sales cycle and increased ACV through refined deal strategy. Desired Skills Startup Experience : Success establishing a sales team at an early stage startup in SaaS, insurtech, or similar B2B business; general startup experience, required. Player‑coach DNA : Proven full‑cycle closer who has also hired, coached, and scaled small teams (Series A → Series B). Domain : B2B rewards/HRtech or health insurance background preferred; experience with benefits brokers/consultants a plus. Channel expertise : Experience building broker/partner programs (brokers, PEOs, marketplaces) and running trainings, spiffs, and joint plans. Builder mindset : Comfortable creating process, not just running it—CRM architecture, playbooks, comp plans, territories, and quarterly business reviews. Strategic + analytical : Can segment markets, size opportunities, set targets, and use data to iterate. Fluent with HubSpot preferred. Communication & leadership : Crisp storyteller, strong executive presence and a collaborative operator who creates alignment across teams. Nice to Have Experience selling health insurance and partnering with brokers (with broad directory of existing connections) Sold to HR/People, Finance, or Total Rewards leaders at SMB–mid‑market Experience launching a new category or benefit Location & Travel Competitive base + variable + equity. Paid parental & family leave. Opportunity to build a category‑defining company with real social impact. Seniority level Seniority levelDirector Employment type Employment typeFull-time Job function IndustriesInsurance Referrals increase your chances of interviewing at JOBS by allUP by 2x Get notified about new Sales Director jobs in Washington DC-Baltimore Area . 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