This week on the Sales Hacker podcast, we speak with Jason Holmes, President and COO of Showpad. Jason specializes in executive sales leadership with CRM, SaaS, and other tech companies. He’s been an executive and/or VP for a variety of household names, such as Marketo, Adobe, and Oracle. He also served on the board of directors for SIM Partners. He's here to chat about one big topic: cash generation.  The GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

75. How To Scale Operations for a High Growth Sales Enablement Company w/ Jason Holmes, COO, Showpad

Hosted by Scott Barker, the GTM Podcast has interviews with well-known tech executives, VCs, and founders. Dissecting a story from their past: what worked, what didn't and how things actually went down. You can also participate by sending in questions for the guests to answer on future episodes!GTMfund is our early-stage venture fund focused on B2B SaaS. We invest in startups with product-market fit, some traction, and are ready for hyper-growth.

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James Kaikis currently serves as the Head of Go-To-Market and Chief Solutions Officer at TestBox, an innovative company revolutionizing the way buyers interact with product demos. Before his tenure at TestBox, James co-founded the PreSales Collective with Yuji Higashi. Under their leadership, the community became a pivotal resource in the presales domain until its successful acquisition in November 2021. James also has a rich history in solution-oriented leadership roles at prominent companies including Salesforce and Showpad.

Discussed in this Episode:The power of presales in driving revenue growth and customer successStrategies for scaling a community-based business from zero to millionsThe future of B2B software demos and how TestBox is leading the chargeLessons learned from a successful startup exit in just 18 monthsInsights on go-to-market strategy, product-led growth, and customer-centricityHighlights: 6:05 - Bootstrapping a community-based business to multi-million dollar revenue. 8:35 - Secrets behind PreSales Collective's rapid growth and successful exit. 11:05 - Transitioning from founder to Chief Solutions Officer at TestBox. 13:35 - The future of B2B software demos and TestBox's innovative approach. 18:35 - The untapped potential of presales in driving revenue growth. 21:05 - Balancing product-led growth with customer-centricity. 23:35 - Lessons learned from building, scaling, and exiting a successful startup. 28:35 - The importance of aligning presales, sales, and customer success. 31:05 - James' vision for the future of presales and B2B software demos. 33:35 - Advice for entrepreneurs and revenue leaders looking to drive growth. 45:05 - One thing revenue leaders believe to be true that James thinks is bull$***. 48:09 - One thing that is working for James in go-to-market right now. 
 Guest Speaker Links (James Kaikis): LinkedIn: https://www.linkedin.com/in/jameskaikis/ 
 Host Speaker Links (Scott Barker): LinkedIn: www.linkedin.com/in/ssbarker/ Newsletter: thegtmnewsletter.substack.com/ 
 Sponsors:Brought to you by Pocus. Pocus turns data into revenue. Combine all product usage and intent signals your team needs to prioritize the best opportunities and take quick action. Pocus helps you build pipeline based on real buying signals, not your team’s best guess (whether it’s landing new logos or expanding existing ones). With Pocus, go-to-market teams at Asana, Canva, Miro, and Loom save 10+ hours a week digging through data to find and close deals with confidence. Create focus for your team with Pocus – see it in action by requesting a demo Pocus dot com slash demo. Brought to you by Synch. Synch is a single platform for all of your Sales & Sales Ops tooling. From using natural language to build dashboards that will make your RevOps lead jealous, to getting forecasting, pipeline management, and lead routing from a single vendor, Synch allows you to spend more time driving the business forward. For more information, head over to withsynch.com.The GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

GTM 90: The GTM Playbook Under Attack and Bootstrapping a Community to Multi-Million Dollar Revenue with James Kaikis

Daniel Ruiz has spent his career driving growth at high-velocity startups, serving as an early employee at multiple YC companies before co-founding Synch. As CEO, he has successfully raised funding from top investors like Haystack and Jack Altman in a challenging market. With Synch, Daniel is on a mission to streamline the go-to-market tech stack, helping revenue teams spend less time on sales ops and more time actually selling. He brings hard-won insights on leveraging investors, landing crucial first hires, and scaling with in-person sales. Most importantly, Daniel is a founder who leads from the front, always eager to hop on a plane to close a big deal.

Discussed in this Episode:The shifting landscape of bundling vs unbundling in the go-to-market tech stack.Key lessons and tactics from Daniel's successful fundraising process.Extracting maximum value from VCs by making specific requests and following up.Why in-person sales and remote work philosophies are crucial considerations for startups.The misguided belief that "outbound is dead" and what's working in outbound sales.How to find and land a critical first sales hire as an early-stage startup.The power of "fake travel plans" for accelerating growth through in-person sales.
Highlights: 
(04:10) - Bundling vs unbundling in the go-to-market tech stack.

(08:36) - Daniel's fundraising process and lessons learned.

(13:39) - Extracting value from investors.

(17:57) - Daniel's "lightbulb moment" on leveraging investors.

(21:10) - In-person meetings and building trust with investors.

(24:35) - Synch's in-person vs remote work philosophy.

(29:52) - When to let go of sales as a founder.

(32:48) - Finding the right first sales hire.

(36:52) - One thing revenue leaders believe to be true that Daniel thinks is bull$***

(41:14) - One thing that is working for Daniel in go-to-market right now. 
Guest Speaker Links (Daniel Ruiz):LinkedIn: https://www.linkedin.com/in/daniel-ruiz-a73818aa/
Host Speaker Links (Scott Barker):LinkedIn: www.linkedin.com/in/ssbarker/Newsletter: thegtmnewsletter.substack.com/
Sponsors:Brought to you by Pocus. Pocus turns data into revenue. Combine all product usage and intent signals your team needs to prioritize the best opportunities and take quick action. Pocus helps you build pipeline based on real buying signals, not your team’s best guess (whether it’s landing new logos or expanding existing ones). With Pocus, go-to-market teams at Asana, Canva, Miro, and Loom save 10+ hours a week digging through data to find and close deals with confidence. Create focus for your team with Pocus – see it in action by requesting a demo Pocus dot com slash demo. Brought to you by Synch. Synch is a single platform for all of your Sales & Sales Ops tooling. From using natural language to build dashboards that will make your RevOps lead jealous, to getting forecasting, pipeline management, and lead routing from a single vendor, Synch allows you to spend more time driving the business forward. For more information, head over to withsynch.comThe GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

GTM 89: Bundling the GTM Stack, Secrets of Winning Investors & Landing Key Hires with Daniel Ruiz

Kyle Lacy spent the last 17 years building, scaling, failing, and winning in high-growth software. He is currently serving the Jellyfish team as their CMO, and before joining the Jellyfish ‘bloom’, He had the pleasure of building a company called Lessonly, employing over 230 people and changed the lives of many more after the acquisition. He has also been fortunate to lead teams at Seismic, OpenView, Salesforce, and ExactTarget. Most importantly, he is the father of two wonderful boys, an energetic dog, and one too many books on World War II. 
Discussed in this Episode:Aligning marketing and sales is crucial for the success of a company, and marketers should focus on numbers and pipeline models from the early stages.Creativity in marketing should be balanced with alignment to sales goals and objectives.Building personal brands can be beneficial, but it's important to be mindful of what is shared on social media and how it may impact professional relationships.When choosing advisors, look for individuals with relevant experience in the stage and industry of your company.Curated dinners and high-quality content are effective strategies for building relationships and engaging prospects and customers.
Highlights:
(04:37) The importance of pipeline models and numbers for early-stage companies.

(06:23) How Kyle gains equal footing with sales leaders

(08:01) Winning over individual sales reps

(09:57) Balancing proactive and reactive marketing

(11:45) The story of winning a 7-figure deal against an incumbent

(15:39) Using donor-choose gift cards in the sales process

(17:00) Converting prospects by asking for feedback and interviews

(18:18) Building a personal brand as a marketer

(21:27) A personal branding misstep that got Kyle in trouble

(24:30) What to look for when bringing on company advisors

(29:10) A widely held belief Kyle thinks is BS

(32:41) A marketing tactic that's working well now

(34:55) Using Lego sets in the sales process

(36:07) Roles Kyle is hiring for at Jellyfish

(31:12) One thing revenue leaders believe to be true that Kyle thinks is bull$***.

(34:51) One thing that is working for Kyle in go-to-market right now. 
Guest Speaker Links (Kyle Lacy):
LinkedIn: www.linkedin.com/in/kylelacy/

Host Speaker Links (Scott Barker):
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/

Sponsors:Brought to you by Pocus. Pocus turns data into revenue. Combine all product usage and intent signals your team needs to prioritize the best opportunities and take quick action. Pocus helps you build pipeline based on real buying signals, not your team’s best guess (whether it’s landing new logos or expanding existing ones). With Pocus, go-to-market teams at Asana, Canva, Miro, and Loom save 10+ hours a week digging through data to find and close deals with confidence. Create focus for your team with Pocus - see it in action by requesting a demo Pocus dot com slash demo. Brought to you by Synch. Synch is a single platform for all of your Sales & Sales Ops tooling. From using natural language to build dashboards that will make your ReThe GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

GTM 88: Know Your Numbers to Create Alignment and Unlock Scale with Kyle Lacy

Prior to founding AudiencePlus, Anthony Kennada served as the CMO of incredible companies like Hopin and Front. He was the founding CMO of Gainsight where he and his team are credited with creating the Customer Success category -- a novel business imperative, profession and software category that helps subscription companies grow sustainably by becoming customer obsessed. By focusing on human first community building, content marketing, live events and creative activations, they developed a new playbook for B2B marketing that built the Gainsight brand and fueled the company’s growth from $0 to $100M+ ARR, and eventual acquisition by Vista Equity at a $1.1B valuation. 
Discussed in this Episode:Owned media is a crucial component of go-to-market strategies, allowing companies to build direct relationships with their audience.Transitioning from a product-first approach to a distribution-first approach can lead to more effective marketing and audience building.The future of media lies in guided journeys and providing value to networks through relevant and personalized content.Building an audience and collecting subscribers can lead to higher conversion rates and provide valuable first-party data for better attribution.It is important to connect brand messaging to the software or product being offered to ensure a cohesive and effective marketing strategy.
Highlights:
(02:58) The Gainsight story: Creating a category and building a brand.

(05:46) The power of owned media in B2B marketing.

(17:51) The evolution of media: from content to software.

(20:41) The challenge of measuring media's impact on revenue.

(27:08) Learning from Gainsight: Successes and missteps.

(38:12) One thing revenue leaders believe to be true that Anthony thinks is bull$***.

(41:00) One thing that is working for Anthony in go-to-market right now. 
Guest Speaker Links (Anthony Kennada):
LinkedIn: www.linkedin.com/in/akennada/

Host Speaker Links (Scott Barker):
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/

Sponsor:Brought to you by Pocus. Pocus turns data into revenue. Combine all product usage and intent signals your team needs to prioritize the best opportunities and take quick action. Pocus helps you build pipeline based on real buying signals, not your team’s best guess (whether it’s landing new logos or expanding existing ones). With Pocus, go-to-market teams at Asana, Canva, Miro, and Loom save 10+ hours a week digging through data to find and close deals with confidence. Create focus for your team with Pocus - see it in action by requesting a demo Pocus dot com slash demo. Brought to you by Synch. Synch is a single platform for all of your Sales & Sales Ops tooling. From using natural language to build dashboards that will make your RevOps lead jealous, to getting forecasting, pipeline management, and lead routing from a single vendor, Synch allows you to spend more time driving the business forward. For more information, head over to withsynch.com.The GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

GTM 87: The Future of Media and Marketing with Anthony Kennada

Katrina Wong is the Divisional CMO / VP Marketing at Twilio Segment. She has a proven track record for launching products in new markets and helping companies move up to the Enterprise. She has also created award-winning integrated campaigns with data storytelling. Prior to Twilio Segment, Katrina worked at Zuora, Salesforce and SAP. She started her career as a management consultant for PricewaterhouseCoopers. With over 15 years of marketing experience, Katrina is passionate about helping companies through stages of substantial growth including helping 6 companies exit successfully – from pre to post IPO as well as notable acquisitions. 
Discussed in this Episode:Marketing plays a crucial role in preparing a company for a successful exit by building awareness, generating pipeline, and creating a compelling narrative.The ability to execute and operate day-to-day is essential for achieving results and improving performance.An operational mindset and execution excellence are key to the success of a company.Building cohesion within marketing teams and aligning on goals and strategies leads to better execution and business results.Hyper-specific messaging and an account-based marketing (ABM) strategy can break through the noise and make marketing efforts more relevant and effective.
Highlights:
(05:54) Unlocking the secrets to successful startups and exits.

(08:19) Operational excellence: the key to startup success.

(13:38) Marketing's pivotal role in preparing for a successful exit.

(20:29) Narrowing down your ideal customer profile (ICP) without breaking the bank.

(22:49) A time machine trip: innovative program implementation at Salesforce.

(25:49) Unlocking potential: a leadership journey.

(27:33) Challenging the 'fire fast' mentality.

(32:35) The power of integrated marketing and team dynamics.

(35:26) Navigating company acquisitions: strategies for success.

(39:00) One thing revenue leaders believe to be true that Katrina thinks is bull$***.

(43:00) One thing that is working for Katrina in go-to-market right now. 
Guest Speaker Links (Katrina Wong):
LinkedIn: www.linkedin.com/in/katrinawong11/ 

Host Speaker Links (Scott Barker):
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/

Sponsor:
Today’s episode is sponsored by The ELG Conference, presented by Crossbeam and The ELG Alliance. The smartest companies are embracing Ecosystem-Led Growth, or ELG. Join us at the gorgeous Proper Hotel in Austin on May 15-16 and hear how the top SaaS companies are leveraging partner ecosystems in their GTM motions aka Ecosystem-Led Growth. Early-bird tickets expire next week. What you'll get at ELG Con:Case studies from companies like Datadog, Cloudera, and more.A chance to tour (and maybe even race on?) Austin's F1 track.Candid, off-the-record conversations — no recordings here.A highly curated group of 200 GTM leaders, 85% director level and above across Sales, Marketing, and Partnerships.Claim your tickets today, including a limited number of special two-for-the-price-of-one tickets. The GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

75. How To Scale Operations for a High Growth Sales Enablement Company w/ Jason Holmes, COO, Showpad

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