JOBS by allUP
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.
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. 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. 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. 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 and improved conversion at 1–2 targeted stages. 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. Player‑coach DNA : Proven full‑cycle closer who has also hired, coached, and scaled small teams. Domain : B2B rewards/HRtech or health insurance background preferred; experience with benefits brokers/consultants a plus. Channel expertise : Experience building broker/partner programs 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. 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. Sold to HR/People, Finance, or Total Rewards leaders at SMB–mid‑market. Experience launching a new category or benefit. Competitive base + variable + equity, paid parental & family leave, and opportunity to build a category‑defining company with real social impact.
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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. 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. 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. 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 and improved conversion at 1–2 targeted stages. 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. Player‑coach DNA : Proven full‑cycle closer who has also hired, coached, and scaled small teams. Domain : B2B rewards/HRtech or health insurance background preferred; experience with benefits brokers/consultants a plus. Channel expertise : Experience building broker/partner programs 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. 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. Sold to HR/People, Finance, or Total Rewards leaders at SMB–mid‑market. Experience launching a new category or benefit. Competitive base + variable + equity, paid parental & family leave, and opportunity to build a category‑defining company with real social impact.
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