SaaSy Talk Unfiltered Ricky and Sean

About The Guest(s): Stephanie Jenkins is the VP of Global Sales at PandaDoc. Prior to PandaDoc Stephanie served as the CRO at rapidly growing Series C startups, and at Glassdoor as the VP of Sales where she scaled the company from an unknown, small-scale start-up to a SaaS recruiting giant (8M →400M ARR). In 2018, she led the team through a successful exit event, an acquisition from Recruit Holdings for 1.2B. Stephanie’s strengths are adaptability, agility, building systems and processes for scale, and creating mission-driven teams. 

Episode Summary: In this episode, Stephanie shares her journey into the tech industry, starting from her desire to move to California and work in the tech industry. She discusses her experience at Glassdoor and the lessons she learned during the company's rapid growth. Stephanie also talks about the importance of work-life balance and how she prioritizes her family while still achieving success in her career. She provides insights into adapting and innovating sales strategies, the impact of her career decisions on her personal life, and her leadership philosophy in motivating her team. Stephanie also discusses the future of Pandadoc and her excitement about AI and its potential in the tech industry.

Key Takeaways:


Stephanie's journey into the tech industry started with her desire to move to California and work in the tech industry, which led her to join Glassdoor and eventually become the Global VP of Sales at Pandadoc.


Glassdoor's growth taught Stephanie the importance of adaptability and experimentation in sales strategies, such as bundling products together and running effective proof of concepts.


Stephanie prioritizes work-life balance and believes in creating a system of regular review of metrics to deliver the right performance while still being present for her family.


As a leader, Stephanie focuses on understanding her team's goals and helping them achieve success both in their careers and personal lives.


Stephanie is excited about the future of Pandadoc, particularly in the areas of AI, contract lifecycle management, and configure price quote solutions.



Notable Quotes:


"It's not the strongest or fastest species that survives, but the ones that can adapt the fastest." - Stephanie


"You have to find the thing that makes you love what you do, that you get up excited to do every day." - Stephanie


"You have to think about who you're working for, what are we doing, how are we helping people, and then how am I helping this company and helping further that mission." - Stephanie



Chapters

00:25 Stephanie's Journey into Tech

03:31 From Sales Beginnings to Global VP

05:17 Lessons from Glassdoor's Growth

07:23 Adapting and Innovating in Sales Strategies

10:56 Exploring Work-Life Balance and Career Choices

14:59 Work-Life Balance in the Tech World

20:28 The Impact of Career Decisions on Personal Life

21:59 Leadership Philosophy and Team Motivation

24:01 Implementing Work-Life Balance in Sales Teams

27:07 The Freedom and Responsibility Model in Sales

30:31 A Week in the Life of a Sales Leader

33:00 Future Aspirations and the Impact of AI

34:09 Legacy and Personal Reflections

35:09 Quick Fire Round: Favorites and Preferences



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About The Guest(s): As the Founder of revenue•x, a GTM and revenue advisory providing fractional CRO services, Neil focuses on helping small and medium-sized businesses build an efficient GTM motion that results in a full pipeline and recurring revenue through people, processes, and platforms.

Neil brings 25+ years of learning within B2B SaaS, technology, consulting and data businesses, where he has helped lead companies through different growth stages, including $0-$3M, $3-$6M, $20-$50M, and $100M-$200M+. Neil's other passion is PORCH, an exclusive community for immigrant entrepreneurs, which he founded with his son Hunter. 

Neil speaks often on the power of community and go-to-networks to help businesses grow and practices what he preaches through his contributions as an Ambassador, and the Chair of the Fractional/Consultant/Advisor group at Pavilion, a Featured Thought Leader at Sales Assembly, and an Advisor at Gartner Sales Community.

His background includes leadership positions at RIWI (CRO), Environic Analytics (SVP of Marketing and Partnerships), Deloitte (VP), Dentus (SVP / Managing Partner),  Rogers (Sr Director), and Nielsen (VP).

Always trying to live by the POP principles (Passionate, Optimistic, Perseverance), Neil prides himself on having a perfect say/do ratio.

Episode Summary: In this episode, Neil shares his journey from working in the corporate world to becoming a fractional CRO and founder of Porch. He discusses the challenges and rewards of entrepreneurship, the rise of fractional roles in the market, and the importance of building relationships in sales and marketing. Neil also talks about his passion for helping immigrant entrepreneurs and the mission of Porch to provide support and resources to this community.

Key Takeaways:


Fractional leadership is a growing trend in the business world, offering companies the expertise of experienced professionals on a part-time basis.


Building relationships and leveraging warm outreach strategies are becoming more effective than traditional cold outbound methods.


Events and in-person interactions are still crucial for building meaningful connections and driving business growth.


Porch is a community for immigrant entrepreneurs in Canada, providing support, resources, and networking opportunities to help them succeed in a new market.


Neil emphasizes the importance of continuous learning and staying up-to-date with new technologies and strategies in sales and marketing.



Notable Quotes:


"I think we all have different risk factors or different things that make us take a jump or not take a jump." - Neil


"Fractional CRO is about getting your hands dirty. I'm doing everything that a full-time CRO would do, just on a part-time basis." - Neil


"Outbound strategies are getting harder and harder. We need to focus on warm outreach and building relationships." - Neil



Chapters

00:09 Neil's Personal and Professional Journey

02:11 Transitioning from Corporate to Entrepreneurship

04:31 The Rise of Fractional Roles and Neil's Current Ventures

04:51 Reflecting on Career Choices and the Impact of COVID-19

10:23 Exploring the Fractional CRO Role and Its Benefits

18:51 Giving Back: BeFractional and Porch Initiatives

23:16 Empowering Immigrant Entrepreneurs: The Forge Community

25:53 Shifting Gears: Go-to-Market Strategies and Business Insights

27:11 The Evolution of Outreach: Embracing Warm Strategies Over Cold

31:56 Navigating the AI Landscape: Strategies for Authentic Engagement

37:16 Looking Ahead: Neil's Focus for 2024 and Beyond

40:00 Quick Fire Round: Personal Insights and Preferences



Revenuex- https://www.linkedin.com/company/revenue-x/

#Befractional - https://www.linkedin.com/company/befractional-org/

PORCH - https://www.linkedin.com/company/porchcommunity/

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About The Guest(s): Don McKenzie is co-founder of Tribe Global Ventures, a B2B focused VC that helps Australian and New Zealand companies scale into the UK and/or the US. Prior to entering the world of VC, Don founded companies including through to the ASX in sectors such as B2B SaaS, construction, insurance services, and consulting. Don’s focus is working with portfolio companies to traverse the predictable problems of high growth using various organisational life cycle development tools.   

Episode Summary: 

In this engaging podcast episode, Don shares his journey from a tech-enthusiast developing algorithms in his youth, to building a successful tech platform and steering through the complexities of entrepreneurship and investment. Delving into the realms of angel and VC investments through his experiences, he emphasises the importance of empathy and authenticity in supporting startups. The conversation highlights the challenges and opportunities in the tech industry, underscoring the significance of product-market fit, effective messaging, and the intrinsic value of learning from failures. Don's passion and insights into building healthy, resilient businesses, and fostering founder growth make for a compelling narrative, offering valuable lessons and inspiration for founders and investors alike.

Key Takeaways:


Founders should prioritise go-to-market strategies and focus on solving real problems that customers are willing to pay for.


Building a healthy organisation with high trust and respect is crucial for long-term success.


Founder transition requires careful planning and a systemic approach to align structure, vision, and mission.


The current investment landscape requires startups to demonstrate real value and solve significant problems to attract funding.


Authenticity and integrity are key to building successful businesses and maintaining strong relationships.



Notable Quotes:


"Your story doesn't matter. It's the counterparties' story that matters. You've got to work out a way to open the door to get into their story." - Don


"Success is not just about passion and vision. It's about the underlying structural elements that often go unnoticed." - Don



Chapters

00:38 Introduction and Guest Welcome

00:46 Don's Journey into Tech and Entrepreneurship

03:54 Insights on Startups and Angel Investing

05:17 The Importance of Learning from Failures

09:37 Challenges Aussie and Kiwi Startups Face

13:39 The Power of Product-Led Growth (PLG)

16:27 Investment Strategies and Go-to-Market Scaling

20:47 Founder to Professional CEO Transition

29:51 The Pitfalls of Founder Transition

32:15 Navigating the SaaS Bubble: Lessons and Strategies

42:00 Investment Strategies and Founder Advice for 2024

47:01 Personal Reflections and Future Aspirations

47:51 Rapid Fire Round: Getting Personal



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About The Guest(s): Andrew grew up in South Africa and built one of the country’s largest healthcare consulting businesses. He has lived, worked, and run businesses on six continents, and has been a salesperson for 25 years.Andrew is the author of The 11th Habit, a Tedx speaker, and a lecturer at Northwestern University’s Kellogg School of Management.Andrew is the founder of Habits at Work, where he and his team help customer-facing teams build relationships, create and leverage trust, and uncover their customer’s

needs beyond what’s on the surface.

Episode Summary: 

In this episode, Andrew Sykes discusses the importance of trust in sales and how it can be built in the first few minutes of a conversation. He shares his journey from being an actuary to starting his own business and becoming a professor of sales. Andrew emphasizes the need for salespeople to be trustworthy and highlights the perception-based nature of trust. He also discusses the current state of sales training and the opportunity to professionalize the sales profession. Andrew provides practical tips for building trust, such as making a positive first impression, finding common ground with prospects, and making promises and delivering on them. In this conversation, Andrew Sykes shares insights on building trust and making a strong first impression. He emphasizes the importance of building trust through small promises and micro-moments rather than grand gestures. Andrew also provides tips on building trust in a boardroom setting, such as greeting each person individually and taking the time to connect with them. He discusses the power of storytelling in sales and how well-told stories can inspire and influence others. Andrew's personal origin story framework is also shared as a tool for building trust. Lastly, Andrew shares his favorite sports team, music genre, movie, and place to visit.

Key Takeaways:


Trust is crucial in sales and can be built in the first few minutes of a conversation.


Salespeople should strive to be trustworthy and focus on building trust with prospects.


The current sales training model often emphasizes quantity over quality, but there is an opportunity to professionalize the sales profession.


Practical tips for building trust include making a positive first impression, finding common ground with prospects, and making and delivering on promises. Building trust is about making small promises and delivering on them in micro-moments.


In a boardroom setting, take the time to greet each person individually and connect with them on a personal level.


Storytelling is a powerful tool in sales as it allows others to see a future that includes their personal transformation.


Craft a personal origin story that includes one sentence about credibility, one about why you do what you do, and one impactful sentence about the privilege of what you get to do.



Notable Quotes:


"Customers decide that they want to buy from you before they decide if or what they want to buy from your company."


"Your job is to stand apart as someone who others view as trustworthy."


"Sales is the conversational art of helping another by speaking their preferred future into existence."


"A well-told story is the gift of allowing others to see for themselves a future that has an opportunity for personal transformation."




Chapters

00:00 Introduction and Background

02:11 The Importance of Trust in Sales

10:00 Building Trust in the First Five Minutes

17:10 The Flaws of the Current Sales System

23:19 Shifting Towards a Customer-Centric Model

29:47 Creating Trust from the Start as an Entrepreneur

37:30 Building Trust in a Boardroom Setting

41:02 Authenticity and Personal Background

43:25 The Importance of Storytelling in Sales

48:03 Legacy and Personal Transformation

50:43 Quick Fire Round



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About The Guest(s): Nicole Brambila is an experienced tech leader and Chief Revenue Officer (CRO) with a diverse background in sales and management. She began her career in the wine industry before transitioning to the tech sector. Nicole has worked at companies such as Eventbrite and Deputy, where she held various roles and gained valuable experience in sales, storytelling, and cross-functional collaboration. Currently, she is the CRO at Medely, a marketplace for nurses, where she is focused on solving human problems in the healthcare industry.

Episode Summary: In this episode, Ricky and Gauri interview Nicole, a seasoned tech leader and CRO. Nicole shares her unconventional journey from the wine industry to tech, highlighting the importance of active listening and empathy in sales. She discusses the human element in technology and the challenges of working in a global role. Nicole also emphasises the value of mentors, both male and female, in her personal growth as a leader. As she navigates her new role as CRO, Nicole focuses on building a strong foundation and shaping the future of the business.

Key Takeaways:


Transitioning from outside sales to inside sales taught Nicole the importance of actively listening, which became a foundational skill in her career.


As a leader, it is crucial to be empathetic rather than sympathetic, as empathy allows for progress and understanding.


Working in global roles taught Nicole the significance of not making assumptions and being open to learning from different cultures and perspectives.


Nicole aims to be more intuitive and trust her instincts as a leader, while also hiring people who are better than her in certain areas.


In her current role, Nicole is focused on building a strong foundation, utilising data as a source of truth, and shaping the future direction of the business.



Notable Quotes:


"Empathising with both the rep, the business, and the prospect is incredibly important, but sympathising with them doesn't actually allow you to progress forward." - Nicole 


"Don't make assumptions and don't assume you know anything. Let them teach you, and you'll be much better for it." - Nicole 



Chapters


00:06 Journey to CRO: From Wine to Tech

02:40 The Human Element in Technology and Career Progression

07:09 Leadership Evolution and Embracing Mistakes

09:49 The Role of a CRO: Challenges and Daily Operations

13:48 Personal Growth and Mentorship in Leadership

20:55 Cultural Differences in Global Roles

32:58 Strategic Planning and Future Goals

35:10 Quickfire Round and Closing Thoughts



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About The Guest(s): Meet Lindsay, the Associate Director of Content & Campaigns at Goldcast. With a knack for creating impactful content, Lindsay focuses on showcasing how B2B marketers can leverage events as top revenue-driving channels. Check out goldcast.io to discover the power of events for brand and business growth.

With a diverse background spanning various industries, Lindsay brings a wealth of experience to the table. From the largest credit union in Alabama to a renowned nonprofit brand and a SaaS company with multiple acquisitions, she's a seasoned content leader and strategist. Lindsay excels in building content engines, fostering team relationships, crafting holistic messaging across channels, and creatively driving business goals.

Beyond her work, Lindsay is passionate about educating others. She's presented on topics like podcasting, content marketing, digital strategy, and nonprofit leadership at prestigious events such as CU Social Media Conference and Together Digital Indy. Lindsay also serves her community as a member of the Junior League of Indianapolis, a writer for Indy Maven, and a supporter of the Humane Society for Hamilton County. She's a graduate of leadership programs like United Way's Leadership United and Indy Hub's 1828 program, showcasing her commitment to personal and professional growth.

Episode Summary: In this episode, Lindsay, Director of Content and Campaigns at Goldcast, joins the show to discuss the power of event and content marketing. Lindsay shares her career journey, transitioning from financial services to non-profit organizations and eventually finding her place in the tech industry. She emphasizes the importance of aligning content with product development and shares insights on leveraging dark social strategies for brand positioning. Lindsay also highlights the value of events in brand creation and awareness, providing tips on planning and budgeting for both large and small-scale events. The conversation concludes with a discussion on the role of podcasts in content marketing and the changing landscape of marketing, including the consumerization of B2B marketing.Key Takeaways:


Transitioning into a new role and industry requires adaptability and a willingness to learn.


Dark social strategies have evolved into evangelism, providing organic opportunities to reach new audiences.


Events are a powerful tool for brand creation, awareness, and lead generation.


When planning events, it's important to align content with product development and consider both large and small-scale options.


Starting a podcast can be a valuable content engine, allowing for the positioning of brand point of view and integration into other marketing channels.



Notable Quotes:


"Dark social has now evolved into evangelism. It's about finding organic opportunities to get in front of new audiences where it doesn't cost a lot of money." - Lindsay 




"Events are a goldmine of content. It's a lever to position your brand, get in front of your audience, and integrate into other marketing efforts." - Lindsay 



Chapters

00:05 Lindsay's Career Journey and Transition into Tech

02:32 The Dark Side of Tech: Pros and Cons

03:47 A Day in the Life of a Director of Content and Campaigns

05:36 Exploring Dark Social Strategy and Evangelism

08:09 Tips for Early Stage Founders on LinkedIn Presence

15:18 The Power of Events in Brand Creation and Awareness

19:20 Strategies for Attending Events and Maximizing Impact

25:37 The Role of Podcasts in Content Marketing

27:42 Leveraging Podcasts for Brand Positioning

29:48 Adapting to a New Role and Industry

31:46 The Changing Landscape of Marketing

32:21 The Consumerization of B2B Marketing

34:02 Advice for Aspiring Content and Campaign Managers

34:11 The Importance of Networking and Project Management

37:25 Reflecting on Personal Legacy and Mentorship

39:55 Quickfire Round



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