Youth Development Director, Waypoint Academy - $150,000/year USD
for section headings like About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule. We must include only sections that have real specific content. We must not repeat job title as heading. Must not put Job ID/requisition numbers as headings; fold minor metadata into short
or drop it. We need to parse the posting. Content: - Intro paragraph about supportive thing, Waypoint Academy description, etc. This is like "About the role" maybe. - Then "What You Will Be Doing" list of duties. - Then "What You Won’t Be Doing" list (maybe not needed? It's still responsibilities but could be part of responsibilities. Could include as part of responsibilities but maybe we can keep as part of responsibilities. - Then "Youth Development Director" heading? Actually the posting includes "Youth Development Director" as title? The job title is Youth Development Director. We shouldn't repeat job title as heading. So we can treat that as part of the role description. - Then "Key Responsibilities" bullet: "Make sure every student in your cohort loves school, grows academically, and builds the character and life skills to thrive." - Then "Basic Requirements" list. - Then "Nice-to-have Requirements" list. - Then "About Waypoint Academy" paragraph. - Then "Working with us": full-time, W2 employee position with immediate access to benefits (link). All roles are year-long positions. The compensation level for this role is $150,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5818-US-Rocheste-YouthDevelopme1.001 We need to include Benefits, Pay, Schedule sections only if posting actually states them. We have compensation: $150,000 USD/year, payment period weekly. That's Pay and Schedule? Payment period weekly is schedule? Actually schedule could be work schedule (full-time). They mention full-time, year-long positions. So we have schedule: full-time, year-long. Benefits: immediate access to benefits (link). So we can include Benefits, Pay, Schedule sections. We must not include placeholder like "commensurate with experience". We have actual numbers. We need to use
for section headings. Use - for any list of duties/requirements/benefits, and
for prose.
We must not output markdown code fences, just raw HTML.
We need to preserve all substantive information, not invent or summarize away detail.
We need to remove cookie/navigation/legal/EEO/equal-opportunity/scam-warning boilerplate, duplicated lines, and application instructions. There's no explicit EEO but there is "Legally authorized to work in the United States" which is a requirement; keep.
We need to drop duplicated lines? Not seeing duplicates.
We need to not put Job ID/requisition numbers as headings; we can fold minor metadata into a short
or drop it. The Job Code line can be placed in a
maybe under Working with us.
We need to decide sections:
- About the role (intro paragraph(s) describing Waypoint Academy, role overview). Could combine intro and "About Waypoint Academy". Might be separate but we can have one About the role section.
- Responsibilities: combine "What You Will Be Doing", "What You Won’t Be Doing", and "Key Responsibilities". Could be a single Responsibilities section with lists.
- Requirements: Basic Requirements list.
- Qualifications: Nice-to-have Requirements (could be Qualifications or Skills). The spec says we can use Qualifications, Skills sections. We'll put Nice-to-have under Qualifications.
- Benefits: immediate access to benefits link.
- Pay: $150,000 USD/year.
- Schedule: full-time, year-long positions; payment period weekly.
We must not create sections with filler. All have real content.
We need to ensure we don't repeat job title as heading. So no
Youth Development Director
. Good.
We need to output only HTML fragment.
Let's craft:
About the role
... intro paragraph(s) ...
Then Responsibilities:
Responsibilities
- Coach the Guides who work alongside you: review performance data, observe them with students, and end every session with specific actions that close the gap.
- Lead one-hour outdoor life-skill workshops where K-12 students build leadership, resilience, teamwork, and communication through adventure-based challenges.
- Run motivation sessions using student analytics and Coachbot data to get every student moving toward their goals and owning their own progress.
- Carry your own student cohort while developing other Guides, so you coach from current experience, not memory.
- Track student satisfaction, goal completion, and Guide performance weekly to catch underperformance before it compounds.
- Make sure every student in your cohort loves school, grows academically, and builds the character and life skills to thrive.
- Do not lecture or tutor students on academic subjects; they learn through self-guided adaptive apps, often with no adult in the room.
- Do not build curriculum or lesson plans from scratch; the playbooks exist; the bar is fidelity and energy, not originality.
- Do not coach Guides on teaching technique; Guides don't lecture, so you coach motivation, accountability, and how they show up with kids.
- Do not lower the bar to keep the peace; you won't pass a student along or smooth over a Guide's underperformance.
- Do not keep kids inside and in their seats; much of the learning happens outdoors, through challenge.
But note: The "What You Won't Be Doing" items are phrased as negatives; we can keep them as responsibilities (what you won't do). It's okay.
Now Requirements:
Requirements
- Willing to work in person at Waypoint Academy in Dripping Springs, Texas
- Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or a related field
- At least 5 years in education, youth development, coaching, outdoor education, or learning and development (L&D)
- Track record of leading a team of 5 or more adults, including hiring and performance-based termination decisions
- Direct experience working with youth ages 5-18 in an educational or developmental setting
- Built, launched, or significantly grew a program, team, school, or outdoor initiative from the ground up, with a specific and measurable example
- Proven use of data and metrics to set goals and drive decisions, not just report results
- Legally authorized to work in the United States
Qualifications (Nice-to-have):
Qualifications
- Master's degree in a related field
- Coached athletics, led wilderness or experiential programs, directed camps, or ran youth programs at a scale that required running cohorts and measuring outcomes
- Left classroom teaching to build or run programs from a different seat: EdTech, tutoring, youth nonprofits, or school intervention teams
- Early-career track record of high personal performance, academic, athletic, or professional, before moving into leadership
- Belief that the standard education model is broken and personal investment in rebuilding it
Benefits:
Benefits
Immediate access to benefits (support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only)
Pay:
Pay
$150,000 USD per year
Schedule:
Schedule
Full-time, year‑long position; weekly payment period
We might also include a short paragraph about Working with us (full-time, W2 employee position, immediate access to benefits, all roles year-long positions, compensation level, payment period weekly, consult link for more details, Crossover Job Code). We already captured benefits, pay, schedule. The Job Code could be a minor metadata; we can fold into a under Schedule or separate small paragraph. Since it's minor, we can add a
after Schedule:
Crossover Job Code: LJ-5818-US-Rocheste-YouthDevelopme1.001
We must not create heading for Job ID. So just a paragraph.
Now check that we didn't repeat job title as heading. Good.
Check that we didn't include any boilerplate like EEO etc. Not present.
Check that we didn't include application instructions like "Hit the Apply button". We removed that.
Check that we preserved all substantive information: intro paragraph about supportive thing, Waypoint Academy description, etc. We need to include that in About the role.
Let's craft About the role paragraph(s):
We have initial paragraph: "The most supportive thing you can do for a kid is hand them something hard and refuse to carry it for them. If that makes you uneasy, stop reading. If it makes you nod, keep going. At Waypoint Academy, core academics run on self-guided, AI-powered adaptive apps that compress the school day into a focused morning. No lectures. That frees you for the work that actually changes a kid's trajectory. Your morning might open with a one-on-one coaching session with a Guide, reviewing student data to find where a cohort is slipping. By midday you're outdoors, leading a workshop that teaches teamwork and resilience through a real challenge. Afternoons shift to motivation sessions: sitting with individual students, learning what drives them, and getting a resistant kid moving toward their goals. You carry your own cohort the whole time, so you stay sharp on the skills you coach in others. You've probably been the square peg in youth development: too data-driven, too results-focused, too willing to take kids outside and let them struggle. This might be the first place that fits. You coach other Guides from day one, and as you deliver results, the standard you set ripples across the whole cohort and your influence over the program grows. You'll see the payoff in person: a skeptical kid who starts owning their progress, a Guide who gets sharper because you told them the truth, a student who walks out of the woods more capable than they walked in. Hold the standard. Take them outside."
Then later there is "About Waypoint Academy Nature-based school that blends rigorous academics with real-world challenges. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!" We should keep the description about Waypoint Academy but remove the "Hit the Apply button" line. So we can combine.
Thus About the role content: combine those two paragraphs (excluding apply instruction). Let's produce:
The most supportive thing you can do for a kid is hand them something hard and refuse to carry it for them. If that makes you uneasy, stop reading. If it makes you nod, keep going. At Waypoint Academy, core academics run on self-guided, AI-powered adaptive apps that compress the school day into a focused morning. No lectures. That frees you for the work that actually changes a kid's trajectory. Your morning might open with a one-on-one coaching session with a Guide, reviewing student data to find where a cohort is slipping. By midday you're outdoors, leading a workshop that teaches teamwork and resilience through a real challenge. Afternoons shift to motivation sessions: sitting with individual students,
for prose. We must not output markdown code fences, just raw HTML. We need to preserve all substantive information, not invent or summarize away detail. We need to remove cookie/navigation/legal/EEO/equal-opportunity/scam-warning boilerplate, duplicated lines, and application instructions. There's no explicit EEO but there is "Legally authorized to work in the United States" which is a requirement; keep. We need to drop duplicated lines? Not seeing duplicates. We need to not put Job ID/requisition numbers as headings; we can fold minor metadata into a short
or drop it. The Job Code line can be placed in a
maybe under Working with us. We need to decide sections: - About the role (intro paragraph(s) describing Waypoint Academy, role overview). Could combine intro and "About Waypoint Academy". Might be separate but we can have one About the role section. - Responsibilities: combine "What You Will Be Doing", "What You Won’t Be Doing", and "Key Responsibilities". Could be a single Responsibilities section with lists. - Requirements: Basic Requirements list. - Qualifications: Nice-to-have Requirements (could be Qualifications or Skills). The spec says we can use Qualifications, Skills sections. We'll put Nice-to-have under Qualifications. - Benefits: immediate access to benefits link. - Pay: $150,000 USD/year. - Schedule: full-time, year-long positions; payment period weekly. We must not create sections with filler. All have real content. We need to ensure we don't repeat job title as heading. So no
Youth Development Director
. Good. We need to output only HTML fragment. Let's craft:About the role
... intro paragraph(s) ...
Then Responsibilities:Responsibilities
- Coach the Guides who work alongside you: review performance data, observe them with students, and end every session with specific actions that close the gap.
- Lead one-hour outdoor life-skill workshops where K-12 students build leadership, resilience, teamwork, and communication through adventure-based challenges.
- Run motivation sessions using student analytics and Coachbot data to get every student moving toward their goals and owning their own progress.
- Carry your own student cohort while developing other Guides, so you coach from current experience, not memory.
- Track student satisfaction, goal completion, and Guide performance weekly to catch underperformance before it compounds.
- Make sure every student in your cohort loves school, grows academically, and builds the character and life skills to thrive.
- Do not lecture or tutor students on academic subjects; they learn through self-guided adaptive apps, often with no adult in the room.
- Do not build curriculum or lesson plans from scratch; the playbooks exist; the bar is fidelity and energy, not originality.
- Do not coach Guides on teaching technique; Guides don't lecture, so you coach motivation, accountability, and how they show up with kids.
- Do not lower the bar to keep the peace; you won't pass a student along or smooth over a Guide's underperformance.
- Do not keep kids inside and in their seats; much of the learning happens outdoors, through challenge.
Requirements
- Willing to work in person at Waypoint Academy in Dripping Springs, Texas
- Bachelor's degree in education, psychology, business, outdoor education, recreation, youth development, or a related field
- At least 5 years in education, youth development, coaching, outdoor education, or learning and development (L&D)
- Track record of leading a team of 5 or more adults, including hiring and performance-based termination decisions
- Direct experience working with youth ages 5-18 in an educational or developmental setting
- Built, launched, or significantly grew a program, team, school, or outdoor initiative from the ground up, with a specific and measurable example
- Proven use of data and metrics to set goals and drive decisions, not just report results
- Legally authorized to work in the United States
Qualifications
- Master's degree in a related field
- Coached athletics, led wilderness or experiential programs, directed camps, or ran youth programs at a scale that required running cohorts and measuring outcomes
- Left classroom teaching to build or run programs from a different seat: EdTech, tutoring, youth nonprofits, or school intervention teams
- Early-career track record of high personal performance, academic, athletic, or professional, before moving into leadership
- Belief that the standard education model is broken and personal investment in rebuilding it
Benefits
Immediate access to benefits (support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only)
Pay:Pay
$150,000 USD per year
Schedule:Schedule
Full-time, year‑long position; weekly payment period
We might also include a short paragraph about Working with us (full-time, W2 employee position, immediate access to benefits, all roles year-long positions, compensation level, payment period weekly, consult link for more details, Crossover Job Code). We already captured benefits, pay, schedule. The Job Code could be a minor metadata; we can fold into aunder Schedule or separate small paragraph. Since it's minor, we can add a
after Schedule:
Crossover Job Code: LJ-5818-US-Rocheste-YouthDevelopme1.001
We must not create heading for Job ID. So just a paragraph. Now check that we didn't repeat job title as heading. Good. Check that we didn't include any boilerplate like EEO etc. Not present. Check that we didn't include application instructions like "Hit the Apply button". We removed that. Check that we preserved all substantive information: intro paragraph about supportive thing, Waypoint Academy description, etc. We need to include that in About the role. Let's craft About the role paragraph(s): We have initial paragraph: "The most supportive thing you can do for a kid is hand them something hard and refuse to carry it for them. If that makes you uneasy, stop reading. If it makes you nod, keep going. At Waypoint Academy, core academics run on self-guided, AI-powered adaptive apps that compress the school day into a focused morning. No lectures. That frees you for the work that actually changes a kid's trajectory. Your morning might open with a one-on-one coaching session with a Guide, reviewing student data to find where a cohort is slipping. By midday you're outdoors, leading a workshop that teaches teamwork and resilience through a real challenge. Afternoons shift to motivation sessions: sitting with individual students, learning what drives them, and getting a resistant kid moving toward their goals. You carry your own cohort the whole time, so you stay sharp on the skills you coach in others. You've probably been the square peg in youth development: too data-driven, too results-focused, too willing to take kids outside and let them struggle. This might be the first place that fits. You coach other Guides from day one, and as you deliver results, the standard you set ripples across the whole cohort and your influence over the program grows. You'll see the payoff in person: a skeptical kid who starts owning their progress, a Guide who gets sharper because you told them the truth, a student who walks out of the woods more capable than they walked in. Hold the standard. Take them outside." Then later there is "About Waypoint Academy Nature-based school that blends rigorous academics with real-world challenges. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!" We should keep the description about Waypoint Academy but remove the "Hit the Apply button" line. So we can combine. Thus About the role content: combine those two paragraphs (excluding apply instruction). Let's produce:The most supportive thing you can do for a kid is hand them something hard and refuse to carry it for them. If that makes you uneasy, stop reading. If it makes you nod, keep going. At Waypoint Academy, core academics run on self-guided, AI-powered adaptive apps that compress the school day into a focused morning. No lectures. That frees you for the work that actually changes a kid's trajectory. Your morning might open with a one-on-one coaching session with a Guide, reviewing student data to find where a cohort is slipping. By midday you're outdoors, leading a workshop that teaches teamwork and resilience through a real challenge. Afternoons shift to motivation sessions: sitting with individual students,