Loren Alhadeff joined DocuSign as its 17th employee and first sales director, helping grow its sales from $2.5 million to over $2.5 billion before becoming a Venture Partner at Madrona, where he now helps founders—especially technical ones—build real sales teams and avoid the common missteps that come with that shift. Outside of venture work, he brings an unusually varied background, having managed local Los Angeles hip-hop artists in college before moving into enterprise sales and investing.