Job Description
We are Skyward.
That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and unified; creative and collaborative; a collection of complementary, not competing talents. And though on the surface we remain relaxed, beneath, a torrent of energy links us to our civic tech mission.
We stand by our values, and we won’t compromise on any of them.
Integrity: We’re conscientious, intentional, and empathetic. Our words and actions align. That’s our character. Please don’t ask us to play another part, we’re poor actors.
Compassionate: If we may borrow a quote from Theodore Roosevelt: “No one cares how much you know until they know how much you care.” Because our team is thoughtful and supportive, caring deeply for each other, our clients, and our work, this comes naturally.
Inquisitive: We remain students by failing openly and turning lessons into solutions.
Unconventional: For us, life isn’t what happens outside of work. Work happens inside of life and our culture erases the line often dividing the two.
Authentic: Made possible only because we embody the values listed above. We’re relaxed and fun yet intensely curious and driven. Team members are placed with thought, care, and precision to ensure that Trust, Truth, and Transparency continue to represent our brand.
Because of that, we continue Onward, Upward, and Skyward.
We need a Senior Advisor, Business Development & Strategy
Do you understand the inner workings of the Department of Homeland Security (DHS)? Do you know how to build trust in high-stakes environments, and see opportunity in the early signals of federal procurement? If you’re passionate about national security, energized by digital modernization, and ready to put your deep market insight to work shaping smarter solutions and stronger partnerships, this role is for you.
Come join us if you’re motivated to learn from others, to learn from mistakes, to be part of a future-looking and growth-oriented team.
Let’s go Skyward together.
What you’ll do:
- Lead business development and capture strategy for priority pursuits across DHS agencies.
- Shape early-phase opportunities through customer engagement, teaming strategy, and competitive positioning.
- Develop and maintain a pipeline of opportunities for DHS market.
- Build teaming arrangements with industry partners to amplify value proposition and enhance pWin.
- Work closely with growth, leadership and our delivery teams to align capture efforts with Skyward’s technical strengths and mission vision.
- Provide deep market insight into acquisition trends, customer needs, and emerging opportunities in cleared spaces.
- Guide internal teams in navigating cleared procurement landscapes, including pre-RFP shaping and partner engagement.
- Establish and expand Skyward’s reputation and network in the national security and homeland missions arena.
- Serve as a strategic advisor on partnerships, contract vehicles, and solutioning approaches to improve win probability.
- Build and maintain strong relationships with DHS customer segments.
- Support efforts required to respond to requests for proposals (RFIs and RFPs).
What we’d like you to have:
- Demonstrated success leading growth and capture strategy, managing a robust portfolio across DHS, with a preference for digital service or IT modernization programs that results in new business awards.
- Deep understanding of federal procurement processes.
- A strong, trusted network of established relationships within DHS organizations and industry partners.
- Experience working within or alongside digital services firms or delivery-focused contractors.
- Excellent communication and executive-level briefing skills.
- Strategic mindset with an ability to operate independently, set direction, and influence across teams.
- Entrepreneurial mindset with a desire to build, not just maintain.
- Demonstrated experience in formulating strategic partnerships to secure new business ventures.
What would blow us away:
- You have operational familiarity with homeland security, especially with CBP, TSA, and USCIS.
- Your uncanny ability to bridge business development and technical solutioning - especially in cloud, DevSecOps, or AI/ML domains.
And now the important part. What we offer you:
- Medical, dental, vision insurance (fully paid for employees)
- 15 days of paid leave
- 7 days of sick leave
- 2 days bereavement leave
- 11 paid Federal holidays
- Up to 40 hours for jury duty
- 401K with 4% employer contribution (and no vesting period)
- Up to 4 weeks of paid paternity and maternity leave
- Company provided laptop
- $5,000 per year for professional development
- $600 per year for technical supplies and equipment
- $2,000 referral bonus
- Life and disability insurance
- HSA and FSA
- Legal Shield and ID Shield Voluntary Benefits
- Opportunity to work in a collaborative, motivated team focused on modernizing government services with cutting-edge technology and innovative solutions. Who says government work can’t be exciting!
$150,000 - $175,000 a year
We believe great work deserves great pay. That’s why we ensure our compensation is not only competitive but also fair and transparent, as required by Maryland law. Expect a salary that matches your skills, experience, and the value you bring to the table — because you’re worth it!
At Skyward, we are committed to creating an environment where everyone, regardless of gender, race, ethnicity, sexual orientation, disability, or background, can thrive. We support flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees, including caregivers and those with unique needs.
Offers of employment with Skyward are contingent upon acceptable results of a background investigation.
Applicants must have the ability to obtain and maintain a Public Trust security clearance due to the nature of our work as a government contractor.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
